


The Intern

by kelseycurtis



Category: The Walking Dead (TV)
Genre: Alternate Universe - Sugar Daddy, Anal Plug, Anal Sex, BDSM, Bondage, Breathplay, Butt Plugs, CEO, Choking, Collars, Daddy Kink, Dirty Talk, Dom/sub, Eventual Romance, F/M, Fetish Clothing, Hair-pulling, Heavy BDSM, Interns & Internships, Japanese Rope Bondage, Masturbation, Mutual Masturbation, Oral Sex, Other Additional Tags to Be Added, Punishment, Rape Fantasy, Restraints, Riding Crops, Rope Bondage, Semi-Public Sex, Sharing, Shower Sex, Spanking, Sugar Daddy, Suspension, Vaginal Fingering, Vibrators, Voyeurism, Workplace Sex
Language: English
Status: Completed
Published: 2017-12-17
Updated: 2018-06-29
Packaged: 2019-02-16 06:13:33
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 21
Words: 34,354
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13048164
Author URL: https://archiveofourown.org/users/kelseycurtis/pseuds/kelseycurtis
Summary: Welcome to another Roxy/Negan AU. Featuring Sugar daddy CEO Negan and Sugar baby Intern Roxy.When Roxy applies for a job, she didn't quite expect the crudeness of her boss or his level of unprofessionalism. But Negan has another kind of job in mind for her.





	1. Chapter 1

The Intern

Chapter 1

Roxy’s P.O.V

I stood in the empty elevator, waiting for it to ding at my stop and the doors to slid open. I was nervous to say the least. Being nervous for interviews was normal sure but for an interview like this, I felt like I was gonna start shaking the second I sat down for the interview. This was the job opportunity of a life time. Sure, it was only an internship but if I made a great impression then they might just keep me. I glanced at the mirrored walls, making sure my hair was in place and my lipstick hadn’t smudged. I still looked fine. I smoothed down the front of my tight blue pencil dress and checked my bag once more for all the unessacary paperwork. 

The elevator dinged as it stopped suddenly. The doors slid open and I stepped out on the top floor. I’d made sure to do my research on the company and the man who would be interviewing me. The CEO himself wanted to do the interviews and from his picture on the website he was quite the looker. I headed over to the front desk where a young blonde was sat down, filling her nails. She glanced at me as I approached and forced a smile.  
“I’m here for the interview,” I spoke.  
She looked me up and down, a small smirk forming. This did not help me feel any less anxious. 

The blonde pressed a button on the black phone beside her and held the phone to her ear.  
“Miss Williams is here for her interview, should I send her in?” She asked.  
After a short pause, the blonde put the phone down and gave me directions to the office. I thanked her and walked off. Now was not the time to get lost. Thankfully I didn’t as there was only one office on this floor. I knocked on the door and waited to be called in. I opened the door to find Mr Handsome sat at his desk. 

He smiled wide, showing his perfect white teeth and got up from his chair to greet me. His office was huge, complete with another door on the right that I guessed contained a bathroom for when he was working late. The man in front of me was tall with dark hair slicked back, hazel eyes and slightly greying stubble across his chin. He was wearing a clearly very expensive black suit and red tie. I glanced around his office once more, taking in some of the more personal items. There was a baseball bat mounted to the left wall. 

I stepped further into the room and closed the door behind me. Negan held out his hand and I took it, his handshake firm. Now that I was closer I noticed a small scar across his left cheekbone. He really was…hot.  
“Thank you for taking the time out of your busy schedule to interview me,” I spoke, flashing him a smile.  
“Not a problem, you want a bottle of water before we start?”  
“Sure, thank you.”

Negan stepped over to a small mini fridge, producing two water bottles. He threw it at me, which thankfully I caught. Ok, he could have just handed it to me. Negan sat back down, unbuttoning his suit jacket. I placed the water bottle on the table before producing my resume. I handed it to him, watching as he scanned over it. After a few seconds, he threw the papers over his shoulder and turned back to me. Panic filled me, was my resume a pile of shit? Well so much for this job. 

“I don’t need to read any of that bullshit. I’ll get all the information I need about you with a few questions,” he said matter of factly.  
I almost scoffed, he just swore in an interview. Either he was way too cocky or was toying with me before he dropped the bombshell that I wasn’t good enough for the position.  
“Sorry, is this a joke?” I asked.  
He smiled again, “fuck no. But I’m glad you’re not going to sit there and accept my bullshit like most of the people that walk through this door.”

On the list of worst interviews, this was summing up to be the top spot.  
“So, you good at typing? Good at writing up reports, answering the phone and emails?”  
“I’m fast and efficient if that what’s you mean.”  
Negan looked me up and down, “I bet you fucking are. How about taking peoples shit? You’re gonna get a lot of that if I give you this position.”  
“I try not to let people get under my skin.”  
“Now, tell me. What exactly are you willing to do to get this position?”

My mouth fell open in shock, it’s like he was quoting directly straight from a cheesy porno. He couldn’t be seriously expecting me to suck his dick in order to get the job? The look on his face told me that’s exactly what he expected. God what a fucking slime ball. Yet doubt washed over me. I really needed this job, I needed the money so badly. I couldn’t keep borrowing from my parents. It was bad enough that I didn’t even have hot water at the moment. How bad could it be? I’m sure most the fucking girls here had sucked his dick to get the job. Especially that blonde at the front desk. 

I met his gaze and grit my teeth, “anything.”  
“Glad to hear it. Well I think I’ve heard about all I need too. Thank you for coming today Miss Williams. You should hear from me within the next week.”  
What? So, he was testing me? God, he was so confusing. We’d soon see how long I could actually stand to work with him. That’s even if I got the job. Negan shook my hand once more before I saw myself out his office. Part of me hoped I wouldn’t get the job. I could always find something else, just the sooner the better. 

I left the office building and headed straight back to my apartment. I dumped my bag on the floor and kicked off my heels before sitting down on the couch. I ran my fingers through my hair, still seemingly wrapping my head around that interview. I glanced at my phone for any kind of messages but nothing. I checked the time and decided it would be a good time for lunch. I headed into the kitchen area and opened my fridge to find hardly any bread or cheese left. Hopefully he would call back and soon. 

After two days of hearing nothing finally my phone buzzed. I grabbed it off the coffee table and answered.  
“Hello,” I spoke.  
“Miss Williams, I wanted to let you know that after some serious thinking I decided that you’re the best person for the position,” came Negans voice.  
I almost dropped my phone and made a stupid school girl noise of delight. I paced my living room, grinning ear to ear.  
“That’s great, thank you so much,” I finally responded.

“How soon are you able to start?”  
“Tomorrow?”  
“That would be great, well I’ll see you tomorrow nine AM on the dot. No later. I don’t appreciate lateness Miss Williams.”  
“Duly noted. See you tomorrow.”  
He hung up and I put my phone down. I couldn’t stop smiling, that job was mine. And thinking about it after the first week or so I probably wouldn’t see or hear from that asshole much. This job was going to be a piece of cake.


	2. Chapter 2

Chapter 2

Negan’s P.O.V

Stopping myself from thinking about Roxy for the past few days had been impossible. She was exactly the kind of girl I was looking for, smart, feisty and hot as hell. She'd looked so fucking good in that dress that i had a hard time maintaining self control. It had clung to her figure perfectly, yet completely covered any of the goods. I could tell she was probably a C cup for her bra size. And even though her legs and arms were skinny, her hips told me she'd be a medium for panties. 

God, I fucking wanted her and I knew she knew. As angry as she had been by my behaviour she had still been willing to suck my cock if I asked her. That would come in handy later. I'd proposition her after a week or more. If she said no then that’s fine, life goes on and I'd just find someone else. If she yes on the other hand, we'd both be in for a fucking treat. I could imagine she liked to be spoiled. And boy would I fucking do that in multiple ways.

First thing I'd probably buy her is a new wardrobe, underwear included. The blue dress was nice and all but clearly the most expensive item of clothing she owned. And even then, it didn’t look that fancy. I glanced at the clock, another five minutes and she should be here. I’d tell her the basics and then Dwight would be in charge of her. But I’m sure I could arrange one to one meetings to discuss her progress.

There was a knock at the door, this knock more confident than her last. I called her inside, taking in her choice of clothing. Tight white long-sleeved blouse, the sleeves a little too short and a few buttons undone at the top giving me a flash of her cleavage. A tight pencil skirt, that accentuated her curves. Fuck. Her legs were covered in what was unfortunately more likely to be black tights. We’d have to change that up to stockings soon enough. Her heels were plain and black as well. Her hair was tied back in a high pony tail. I wonder if she liked having her hair pulled.

Thankfully for her sake she was on time. I motioned for her to take a seat, which she took the same chair she had for her interview.  
“So today I’ll show you the basics, introduce you to the people you’ll be working with and then it’s off in the deep end,” I explained.  
Roxy cocked her eyebrow in a way that said ‘hmm figures’ before crossing her legs. I forced my eyes back to her face. Normally I was much more controlled than this but Roxy seemed to be breaking down that wall and that would not do. 

My thoughts wondered to her legs, wondering how they would look in stockings…wrapped around my waist or even my face.  
“Alright so I already have a report I’ll need you to type up and I’ll need it done before lunch time. You think you can do that?” I asked.  
“Sure,” she shrugged.  
I pulled the papers from my desk and handed them to her. She scanned through them before putting them on her lap. 

“Alright so let’s get you to a desk,” I announced.  
Even if I’d much rather have her over my desk. I got up and went around to her side of the desk. She got to her feet, holding onto the pile of papers. I led her out of my office and to the other side of this floor. There a bunch of desks were set up, each with a laptop. I’m sure Roxy would add her own personal items soon enough. I found Dwight at his desk, his blonde hair tied back in a bun. He looked up from his work and smiled. 

I introduced the two of them and explained to Dwight what was needed of Roxy. She was in good hands. Unfortunately, I couldn’t stick around her any longer as I had some work of my own to do before lunch time. A few phone calls to make and a meeting. Hopefully I’d be able to check in on her sometime today. 

\---------------------------------------------------------------------------

Unfortunately for the rest of the week I was unable to drop by and see how Roxy was doing. Thankfully now it was Friday and I had the perfect opportunity. There was a local bar that most co-workers went to after work ready to unwind for the weekend. I’m sure Dwight would have told her about it. I packed up my things and headed out of the office. I dumped my briefcase in my car before driving to the bar. I parked and headed inside. There was a quieter section towards the back and I found Roxy there. 

She was unsure how to handle this situation, that much was obvious. Finally, she smiled softly, deciding it was best not to be confrontational on the first week. Although I still remember the way she looked at me when we’d first met and that gave me all the confidence I needed.  
“So, you survived your first week, want a drink to celebrate?” I asked.  
“Why would I turn it down when you’re buying?”  
“Smart woman. So, which do you prefer beer or cocktails?”  
“How about shots?”  
There was a small sparkle in her eye as if she wanted to challenge me. I’m pretty sure I would be able to drink her under the table easily.

“Alright, but I don’t want to be carrying you home tonight,” I smirked.  
I brought two shots each to start off with. We had no trouble downing both of them one after the other, although Roxy grimaced as the alcohol burned her throat.  
“You wanna stop now before you do some damage?” I joked.  
“It'll take more than that.”  
Roxy ordered the next round and again no trouble at all, if anything it was just making us more comfortable and confident around each other.

“So after your first week, how do you feel?” I asked.  
“The works fine, shame you were too busy this week though.”  
I smiled to myself, “so if you weren’t here tonight what would you be doing instead?”  
“Oh jeez now I have to tell you how boring I am.”  
“I’m sure it can’t be that bad.”  
“Well I wouldn't really be doing much honestly, perhaps reading if my electricity has been turned off. Or I might be round my friend Gwens apartment, she's got a husky called Zeus. And what about you?”

“Sat at home with a glass of Scotch wishing i had some more...pleasurable company. You don't have a boyfriend?”  
“You don't have a wife?”  
“Do you see a ring on my finger?”  
“Do you see one on mine?”  
We smiled at each other before taking a sip from our drinks. I guess now would be a good time as any to pop the question.

“You want to change that? Change your lonely weekends?” I asked.  
Roxy stood there in shock, remaining silent.  
“If you say no that’s fine, I’m not gonna fucking fire you for it. Life fucking goes on,” I continued.  
“And what if I say yes?” She asked.  
“Then we'll need to discuss the rest somewhere more private.”  
“Where exactly did you have in mind?”  
“My office.”

Roxy downed the rest of her drink for extra confidence and then got to her feet.  
“After you,” she spoke.  
I smiled and got to my feet, leading her out of the bar and to my vehicle. The journey was short and silent. She was probably a mixture of emotions, not that I could blame her. She still had the option to say no at anytime.


	3. Chapter 3

Chapter 3

Roxy’s P.O.V

We made our way up to his office, the journey quiet. I didn’t know what to think. He said nothing would happen if I said no and I hope he meant that. I'd hear him out, think it over and then give him my answer. He held the door to his office open for me and let me go inside first. He motioned for me to take a seat on the black leather couch, whilst he pulled up a chair so he was sat opposite me. I removed my coat and sat down. God this thing was comfy. Negan leaned forward, his hands pressed together. It felt like I was back in the interview all over again only this time he needed to pitch himself to me.

“I'd like to start sleeping with you and each time I'd pay you $400 for it. You’ll get $200 tonight even if you say no,” he explained  
“This makes me feel like a prostitute.”  
“I can assure you its not like that. I'd like to consider myself a sugar daddy. I’d like to start buying you gifts, perhaps paying off your bills too.”  
“Why?”  
“Why you?”  
I nodded.

He shrugged, “I like you, you’re very interesting, you don’t seem to take anyone’s shit which is rare for an intern and your hot as fuck,” he explained, “I want to take care of you, i think this job is beneath you. Your smarter than typing up shit I’m too lazy to do myself.”  
I felt my cheeks burn and a smile tug at the corners of my lips, “really?”  
“Fuck yeah.”  
So, he had somewhat of a sweeter side. I hid my smile a little with my hand. I think I quite liked this arrangement. There didn’t seem to be any downsides. I was the one that received the most benefits, I get to fuck a handsome rich guy a few times a month, he pays me and will probably buy me gifts.

I was in.  
“Well I've thought about it and my answer is yes. I'd like this, a lot,” I responded.  
“Good. Would you be ok if we started tonight?”  
“Sure.”  
“Take your clothes off for me.”  
I swallowed before getting to my feet, I kicked off my heels and began to unbutton my shirt slowly, taking my time with each button. I’m sure he wanted some effort put into this. Not that I’d exactly been adventurous with my few sexual partners.

I untucked my shirt from skirt and pulled it off, dropping it to the floor. Negans eyes fell to my chest, his eyes taking in every inch of me that was revealed to him. I turned around and unzipped my skirt before pulling it off. Shame I hadn't work stockings, tights were a lot less sexy. Although the way he was looking at me made me feel anything but unattractive. He looked like he wanted to devour me whole. I removed my tights and stood there in my unmatching, boring underwear. 

Negan’s fists were balled, one covering his mouth as if he were in deep thought. His eyes had darkened with lust and I was surprised he was able to control himself. Although his demeanour from earlier had completely changed, there was no more fun, goofball Negan. This man was completely and utterly in control. He watched me like a predator would watch its prey. Once he'd gotten a good view of my front her made a ‘turn around’ motion with his finger. I did as I was told, feeling like refusal would be a bad idea.

“You can take the rest off now,” he spoke his tone different, more authoritative.  
I unhooked my bra and let it drop to the floor before removing my panties. He held his hand out for them and I hesitantly put them in his hand. Why the hell was I suddenly embarrassed? Negan put them in his pocket and smiled softly.  
“Well look at you, fucking gorgeous,” he grinned, running his tongue over his teeth.  
I wonder how his tongue would feel on my clit. I felt my blush deepen at the thought.

“Sit back down, baby girl. I want you to touch yourself for me,” he spoke softly, yet the order was clear.  
I sat back down, the leather cold against my skin. I couldn't remember a time I'd done something like this before. I was torn between shying away from his gaze and wanting to put on a show for him. I was completely exposed to my boss. Getting cold feet now was probably not a great idea. My hand wondered between my legs, my fingers brushing against my clit. I took a sharp intake of breath at the contact, closing my eyes. 

I heard him tut, which made me open my eyes once more. He wanted me to look at him the whole time.  
“I’m going to ask you a few questions, just so I have a better understanding of your interests,” he spoke.  
I nodded, biting my lip as I continued to circle my clit. My hips bucked a little and I moaned softly. Negan smirked, glancing down before his gaze returned to meet mine. It had been a while since I’d had sex or even masturbated so it was unlikely I was going to last long. I wanted him to touch me, I wanted his hands all over me. 

“Did you want me sexually before tonight?” He asked.  
God, I was probably as red as a tomato right now. Of course, I had. What woman in their right mind wouldn’t? I nodded. His authoritative side took over once more and he sat back in his chair, his eyes narrowed.  
“You’ll speak when spoken too, baby girl,” he threatened.  
“Yes.”  
“And you’ll call me daddy when you answer me.”  
As if I couldn’t feel more ridiculous, now he wanted me to call him daddy. I felt like I might die of embarrassment at any moment. 

“Yes, daddy.”  
“Good girl.”  
I felt my heart swell at the praise and became confident in my actions once more. I continued stimulating my clit before my fingers slipped lower and I pushed two fingers inside my wet heat. I moaned as I started a slower pace, not wanting to rush this.  
“What did you think about? Don’t skip out any details?”  
And here comes the embarrassment again. I felt like a yoyo of emotions and he wanted me to somehow get off like this.  
“Uhm…excuse the typicalness of the fantasy, but you fucking me over your desk,” I confessed.

“I’m sure I can arrange that.”  
I bit my lip, holding back a moan. I increased the pace with my fingers, which were now completely coated in my arousal. I brought my other hand down and resumed rubbing my clit. I could feel a tightness slowly building in my stomach. I wasn’t sure how much longer I could last especially with how he was looking at me. I hope he touched me soon. My need for him had grown and I could only plead with my eyes.  
“And how about a fantasy that your ashamed of?” He questioned me again.  
I let out a pathetic sounding whine, my eyes threatening to fall shut at any moment. 

I slowed my pace down so that I could actually think. I had to look away from him in shame as I found my answer.  
“I like the idea of completely giving up all control to someone else. Letting them do what they want to me,” I admitted.  
“You like to be the centre of attention, used…spoiled.”  
“Yes…daddy.”  
I noticed the large bulge in the front of his trousers, licking my lips instinctively. God, I wanted to see his cock, wanted to sink myself down onto it and ride him like a fucking stallion. My pace sped up once more at these thoughts. 

I moaned again, getting closer and closer with every thrust of my fingers. I made a come-hither motion with them, curling them against my g-spot. A few more strokes and I reached my climax, cursing and moaning as I tightened around my fingers. Once I recovered a little from my orgasm I noticed the unhappy look on Negans face. Was this not what he wanted? I felt like a child about to be scolded by an adult.  
“Did I give you permission to cum, baby girl?” He asked.  
“No, daddy.”  
“You bear that in mind for next time. I’ll let it slide…just this once.”

I grabbed a tissue and began to use it to clean my fingers off but he stopped me with a tut.  
“Let daddy have a taste of you,” he spoke.  
For the hundredth time this evening I blushed, holding my fingers out to him. He leaned forward in his chair and took the digits in his mouth. His tongue swirled around my fingers, cleaning them thoroughly. And just like that I was aroused again. Negan met my gaze and smiled, releasing my fingers with a wet pop.  
“You can get cleaned up in the bathroom. I’ll call my driver to take you home,” he explained.

Oh. So, he didn’t want to have sex with me. Was it because I had cum without permission and this was my punishment? Figures. I gathered my clothes and entered his bathroom. I cleaned myself up the best I could without taking a shower. I’d rather do that in my own apartment. I redressed and went back into his office. He got to his feet and kissed my cheek.  
“The money will be in your account by tonight. I’ll see you next week,” he spoke.  
I smiled softly, still disappointed that he hadn’t even so much as touched me tonight. It was my own fault, I should have guessed that I had to ask permission what with his preferred pet name. This arrangement was going to take some getting used to.


	4. Chapter 4

Chapter 4

Negan’s P.O.V

I sent Roxy the money through her PayPal account, as well as a little extra just as a kind gesture. The rest of the weekend was uneventful and for once I was desperate for Monday to come back around. I’d ordered a few things that would come in handy as well. Some new matching underwear for her as well as some toys. Vibrating panties, a pink glass butt plug. We would buy more later. 

I scanned over the report Roxy had typed up before the weekend. Everything was in order but I had another report for her to type up. I had her called to my office and waited patiently. I knew she had been disappointed the last time because she hadn't been able to fuck me. It was nice to know she was eager. But she still needed to earn it before I gave it to her. We'll see if she could do that today.

Roxy entered my office, closing and locking the door behind her. She was wearing a simple black pencil dress, with plain heels to match. She smiled and walked over to my desk.   
“You wanted to see me?” She asked.  
“I've got another report for you to type up. Did you get the money I sent through?”  
“Yes, thank you.”  
“Now this report is very special and I need it done in two hours.”

“Sure,” Roxy replied.  
“Would you be able to do it here, on my computer?”  
Roxy smiled softly and nodded. She knew exactly where this was going. I motioned for her to come around to my side. As she did, I thought it would be a good time to get out her first present. I produced the rectangular black box from my drawer and put in on the desk. Roxy glanced at it and I slid it closer to her.  
“Having things brought for me is going to take some getting used to,” She spoke.  
“Well I would get used to it quickly.”

Roxy hesitantly took the box and removed the lid. Her eyes widened a little and pulled out the small pink viberator. The viberator was the next size up from a bullet vibe. It didn’t come with any attachments, it was just plain and simple. Although it did have seven different vibrations. Roxy’s cheeks had turned a light shade of pink and she placed it carefully back in the box.   
“Uhm, thanks,” she said.   
“You don’t like it?”  
“I haven’t used one for a few years and I didn’t think my first gift from you would be something quite like…this.”  
“And what did you think I would get for you instead?”

She shrugged, “maybe some nicer underwear. My underwear drawer could do with some excitement.”  
“Perhaps next time. So, you think you could do this report?”  
Roxy’s shyness was replaced with confidence, “you know I can.”  
I smirked. She had no idea what was coming.   
“Elbows on the desk please,” I ordered.  
I noticed how her shoulders slumped, this report wouldn’t be so simple. I pushed myself back in my chair so she had the room she needed. Roxy bent over my desk, her elbows resting on the wood like I had asked.

I placed the papers next to her before pulling my chair back closer to her. It was tempting to have her sit on my lap whilst she did this, but that could lead to other things. Things she hadn’t earnt yet. With her rear stuck out so tempting in front of me, I had to hold back from spanking her. Even if she did deserve it for cumming without permission last time. But I didn’t want to scare her off with things like punishments just yet. Instead Roxy had begun typing, the keys clacking quickly under her fingers whilst she worked. 

I leant forward a little, letting my fingers trail up the length of her bare legs. The typing paused and I felt her shiver under my touch.   
“If you stop baby girl then I stop, understood?” I asked.  
“Yes…daddy.”  
Roxy began typing again, slower this time. I continued my way up her legs until I reached the hem of her dress, which I pushed up and over her rear. Roxy was wearing plain black panties. I pulled them down so they pooled around her ankles. I licked my lips, taking a calming breath so that I didn’t lose my self-control. 

She was already a little wet. Well I’m sure I could change that. I removed the vibe from the box and pressed the single button, turning it on the first and lowest setting. It was fairly quiet but I noticed how she flinched a little at the sound. I ran the tip of the vibe along her slit, teasing her at first and letting her get used to the feeling. Roxy let out a shaky breath, the sound of typing stopping once more. I tutted and pulled the vibe away. Regaining her composure, she began typing again. This time I pressed the toy to her clit, holding it there and watching as she twitched and shifted for the best possible feeling. 

“That feel good baby girl?” I asked.  
“M-more,” she whined.  
“Hmm, seems like you’re going to need to learn patience as well as manners.”  
The vibe remained where it was on the same setting. I smiled to myself as she whined once more. I’m sure later into our relationship this situation would be reversed. I’d see how many times I could make her cum just with this until she couldn’t take it anymore. Her breathing was heavier now and her typing was continuing to slow down as she lost focus. 

After another few minutes, however she managed to put the pleasure to the back of her mind and focus on typing up the report. Now it was time to increase things. I pressed the button once more, increasing the intensity of the vibrations. Roxy moaned and arched into the toy.   
“You have no fucking idea how hard it is to restrain myself right now baby girl,” I spoke.  
“Well then don’t,” she replied.  
I chuckled, “now where’s the fun in that?”  
She made a frustrated sound. I pressed the tip of the vibe against her clit harder, making her moan once more. 

Another five minutes and she finally finished the report, now fully leaning back into the vibe. I shook my head and turned it off before pulling it away. She turned her head to look back at me, her cheeks flushed, her eyes heavy and her mouth slightly agape.   
“You didn’t think I was going to let you cum, did you?” I asked.  
Roxy frowned, looking hurt.   
“After cumming without my fucking permission last time, I thought this was a fitting punishment. Besides would you really want to cum right here in my office? Because I can tell you’re not quiet baby girl. Everyone here would think I had a whore in here and imagine their surprise when you walked out of here. Would you really want that baby girl?”

Roxy turned around to face me, still looking disappointed at the lack of orgasm.   
“I can be quiet,” she insisted.  
“You really want to prove it? Because I don’t give a fuck what other people think about me. But you’d be the talk of the office.”  
“Please, I’ll be quiet.”  
“Let’s hope so, or otherwise we’ll have to get you a gag…or perhaps we will anyway. I think you’d look good like that.”  
Roxy blushed, biting her bottom lip at the fantasy.   
“Let me read over the report and if it’s perfect then and only then will I let you cum,” I bargained. 

Roxy turned around and sat on the edge of my desk off to the side so I could read over the report. Luckily for her it was almost perfect. I’d let one typo slide. I turned the vibe back on to the second setting and pushed it back against her clit. Roxy moaned, arching into the feeling once more. It wasn’t long until her thighs were shaking and she brought her hand up to cover her mouth so that her moans were muffled.   
“Cum for me baby girl,” I spoke, finally giving her the permission she needed.  
Roxy reached her climax, pressing her hand harder against her mouth as she let out a shrill cry. The vibe continued to stimulate her through her climax, Roxy moaning until overstimulation set in and she jerked away. 

I turned the vibe off and produced a pack of baby wipes to clean it with before putting it back in its box. Roxy was breathing heavily, her legs still shaking a little. I handed her panties back to her and helped her back into them. I pulled the skirt of her dress back down before helping her off the desk. She clung to me for a little whilst she regained her balance. I kissed the top of her head and smoothed her hair down. She decided to sit back down, only opting for a chair this time. Her breathing had regulated and the redness in her cheeks had gone down to a soft pink. 

Her next question caught me a little of guard.  
“Why won’t you touch me?” She asked, hesitancy clear in her voice, “am I not exactly what you wanted?”  
“No baby girl. Your perfect. I just like taking my time with things like this. And besides I’ll touch you and fuck you when you earn it.”  
She bit her lip at this, “you think I can’t take it?”  
“Not yet. And before your stubborn side takes over, I think you should get back to work.”  
Roxy narrowed her eyes at me, a smirk playing at the corner of her lips, “yes sir.”  
“Careful, baby girl.”  
She got to her feet and grabbed her present box before leaving my office, taking one last look at me before she closed the door. Perhaps next I could convince her to wear vibrating panties in a meeting. I’m sure if not I’d found something else just as fun.


	5. Chapter 5

Chapter 5

Roxy’s P.O.V

I sat down at my desk and went to work. The day passed quickly without much incident and thankfully it was Friday too so there was the weekend to look forward too. An hour before the end of my shift I got an email from Negan that simply said, ‘come to my office.’ I bit my lip, I wonder what he had in store for me today. I closed down the email and locked my computer out of fear a co-worker might stumble across the message. I left my desk and headed to Negans office, knocking on the door before he called me inside. 

I entered, closing the door behind me. I took a seat and crossed my legs. He smiled softly, his eyes lingering over my bare legs before finally he met my gaze.  
“I was wondering if you had any plans tonight,” he spoke.  
“Not yet I don’t.”  
His smile grew, “dinner?”  
“I don’t see why not.”  
“Good, we’ll wait for everyone to leave the office before heading out ourselves.”  
“And where exactly are you taking me?”

“Caxton Grill.”  
“You managed to get a table there? That place has been fully booked for weeks.”  
“I have experience in making people give me what I want.”  
I bit my lip at that comment. He sure fucking did. It dawned on me that he’d booked a table before I’d even given him an answer. He was that sure of himself.   
“You were that sure I’d say yes?” I asked.  
“You have yet to turn me down for anything I ask.”  
Maybe out of spite I should turn him down the next time. 

“One other thing,” Negan spoke.  
Here comes the catch. Of course, it wasn’t going to be just dinner.  
“I want you to wear these,” he slid over another small sleek black gift box.  
I braced myself before removing the lid. Inside was a thin black lacy pair of panties. Ok. I could wear these no problem. That’s when I saw the small black viberator next to them. The panties came with a little slot for the vibe to sit in. And I’m guessing he had the remote too. This situation would be way more public than last time. There would be people around…strangers sure but people all the same. 

Negan leant forward in his chair, “you can always say no if you’re not comfortable.”  
I met his gaze, not wanting to back down from this. I wanted to prove to him that I could do it.   
“You mind if I change in your bathroom?” I asked.  
He smiled, “not at all.”  
I took the panties and vibe into his bathroom and switched underwear. The small bullet vibe was resting against my clit but with it off it didn’t pose as a problem. I’m sure that would change later. 

Finally, once the office was practically empty all except the cleaners, Negan and I left together. He led me down to the parking lot and opened the passenger side car door for me. Of course, he had a fucking convertible. And I’m sure he had a few other cars. We sat in comfortable silence for the journey. Negan parked and opened the door for me, giving me his hand to help me out. He led me inside and gave his name to the front of house before we were lead to the back of the restaurant. This area was thankfully quieter than the rest of the place. It was also very fancy and I felt out of place. 

I looked at the menu and my eyes widened at the prices. No way I could afford any of this. Negan wasn’t looking at the menu however, one hand was in his trouser pocket, probably toying with the button of the vibe.   
“You decided what you want?” He asked.  
“I’m still recovering from the prices.”  
“Why? You’re not the one paying. As your daddy, it’s my job and pleasure to spoil you.”  
“And I’m still getting used to it. Perhaps I’ll have the chicken, what about you?”  
“Steak for main, Pumpkin soup for starter and Chocolate, Crème and Caramel Fraiche.”  
“You’ve eaten here before, haven’t you?”  
He shrugged, a smile playing at the corners of his lips, “a few times.”

I put the menu down, “in that case, I’ll have what you’re having. I’ll trust your judgement.”  
“Good girl.”  
I felt heat pool in my belly at his words. The waiter arrived and asked for our order. The viberator came to life on the lowest setting, earning a soft sound from me. I masked it with a cough, earning a concerned look from the waiter.   
“You alright baby girl?” Negan asked.  
I nodded, I’m sure if I’d spoken it would end up turning into a moan. Negan finished relaying our order and the waiter left. Thankfully Negan turned the vibe off after that. 

“If you make it through dinner baby girl, would you like to come back to my place tonight?” He asked.  
I looked at him with surprise, he wanted me to come back to his house, meaning he probably wanted to finally have sex with me. He wanted to touch me and I would finally get to touch him. I almost let out an excitable noise but managed to hold it back.  
“I would,” I spoke as casually as I could manage.   
“I thought you might, but that’s only if you can make it through dinner. If not, I’ll just drop you back at yours.”

So somehow, I was meant to make it through three courses without cumming. I huffed before taking a sip of my wine. Our first course arrived within fifteen minutes and thankfully the vibe stayed off whilst I ate my soup. Had the vibe been on I could imagine that I would have spilled soup everywhere. However, Negan wasn’t going to make this easy for me tonight. When the waiter returned to collect our empty bowls, Negan began asking the waiter about the different wines on the menu. The vibe was turned on again, this time more intense. I closed my eyes, gripping the edge of the table. I whimpered and bucked a little, grabbing the attention of both Negan and the waiter.  
“Are you alright miss?” He asked.  
“Could I perhaps get some water?” I managed.   
“Of course.”

Negan kept the vibe going and I moaned into my fist, muffling the sound from anybody nearby. The waiter was quick to come back with a jug of water and two glasses, before returning once more with our mains. I could feel my orgasm building and bit my lip, my cheeks feeling like they were literally burning. As my orgasm neared Negan turned it off, leaving me on the edge. I whined, rubbing my thighs together in the hopes of some sort of the friction to relieve myself.   
“Remember what I said baby girl,” he reminded me.   
I let out a shaky breath to calm myself and focused on the steak in front of me. Thankfully mine was smaller than Negans or I don’t think I’d be able to make it to dessert in two ways. 

“You think he knows, baby girl?” Negan asked, “knows that your so fucking desperate to cum in front of all these people? Only a slut would be that desperate.”  
I felt unable to respond, like perhaps if I just remained silent, if I was a good girl then he would change his mind and let me cum.   
“You’ll speak when spoken to baby girl,” he snapped.  
“I hope not daddy,” I replied softly.   
“I wonder how fucking wet you are right now, I bet your panties are soaked through.”  
He began cutting into his steak, acting as if nothing had happened.   
“Maybe we should play this little game during a meeting. Imagine the look on your co-workers faces if they found out the real reason your cheeks were flushed and you kept biting your lip,” he spoke. 

“Maybe I’d have to pretend the remote in my pocket right now was the projector remote, pressing the button over and over when the slide wouldn’t change. Maybe someone would take it off me and try it for themselves. By then it would probably be on the highest setting. Probably enough to make you cum right there and then,” he continued.  
I held back a moan at the fantasy, swallowing hard instead. It’s like this man had a front row seat in to my brain. Half the fantasies I found hot I wouldn’t dream acting out…not until now at least. It seemed this man was bringing out the filthier side in me. Dinner was soon over and we moved on to dessert. Negan only turned the vibe on one last time when he was paying for dinner. 

It was only on the lowest setting so I was just about able to handle it. Once the waiter left for the final time Negan turned it off once more and took my hand in his, bringing it to his lips.   
“Such a good girl for me. I think it’s time we headed home, don’t you?” He spoke.   
“Yes…daddy.”  
Negan led me back out to the car before starting the engine and driving us to his place. I could barely contain my excitement. I didn’t even think about the fact I didn’t have an overnight bag. Logic and reason had been completely thrown out the window. Tonight he was going to make me his and that’s all that mattered.


	6. Chapter 6

Chapter 6

Negan’s P.O.V

I parked the car in the drive way and got out, going around to the other side of the car to get the door for Roxy. I took her hand in mine and led her up the steps and to the front door. I unlocked it and pushed the door open. I let Roxy step inside first, following her in and turning on the lights. She was looking around the hallway, taking in every detail. It was obvious by the look on her face my place was much nicer than her own. I led her into the lounge which joint on with the kitchen. She was still looking around like a kid does at a zoo. 

I laced my fingers with hers and led her to the bedroom. She turned to face me, waiting for me to make the first move. I cupped the back of her head, my fingers in her hair. I pressed my lips to hers, our first real kiss. She pressed herself against me, desperate for me to touch her, for me to make her cum. I wrapped my other arm around her waist, holding her in place whilst I continued to claim her lips with mine. I nipped at her bottom lip, earning a soft moan from her.   
“Tell me what you want baby girl,” I spoke.   
Her cheeks slowly grew red, she was so fucking cute when she was embarrassed. 

“Touch me please,” she breathed.   
“Specifics baby girl. You want daddy to hit all the right spots, don’t you?”  
“I want to feel your teeth on my neck, your tongue on my…clit.”  
“That can be fucking arranged.”  
I kissed her once more before kissing a trail down to her neck. She arched into me so I had more access to her neck. I gently nipped at the skin, making her take a sharp intake of breath. She really was going to be soaked by the time I reached her panties. I continued to tease her with soft nips before finally sucking a purple mark into her flesh. 

Roxy moaned, her nails digging into my shoulder for the first time this evening. She’d be able to cover it up with makeup although I liked the idea of everyone at work knowing she was mine. I spun her round so her back was now facing me. I found the zipper of her dress and slowly pulled it down. Her skin turned to gooseflesh from her skin being exposed to the cold air and the building anticipation. I placed a soft kiss at the base of her spine, before pushing her dress off her shoulders. I trailed my fingers down her spine, stopping momentarily to unclasp her bra. I grabbed a handful of her rear. I couldn’t wait to mark her ass with my handprints but that could wait. 

I spun her back around to face me before cupping her breasts. She arched into my touch once more, desperate for everything I could give her. She whined when I tugged on her nipples.  
“Patience baby girl. Daddy wants to take his time with you. We've both waited long enough for this so I need to see every inch of you,” I spoke.  
As my hands left her body again she huffed, clearly annoyed. She'd learn patience eventually. I removed my jacket, draping it over the back of a chair before I removed my tie. It was tempting to tie her hands together but again that could come another night.

I unbuttoned my shirt, removed it and folded it neatly. Her eyes travelled across my body. She bit her bottom lip her eyes filled with need. I felt a swell of pride in my chest. Not bad for an older man. I kicked off my shoes and socks before working on my belt. Roxy looked like she wanted to pounce on me but she managed to keep control as I finally removed the last pieces of clothing from my body.   
“Lie down on the bed,” I instructed.  
Roxy practically threw herself onto the bed, getting in to a comfortable position. I climbed over her, leaning down to kiss her again.

“Can I touch you please daddy?” Roxy asked.  
“Of course, you can.”  
Roxy’s fingertips ran across my chest, mapping out various patterns before trailing further down. She wrapped her hand around my cock, watching me closely to see if every move she made was still ok.   
“However tonight is all about you,” I spoke.  
I kissed a trail down her chest, pausing to take a nipple between my teeth. She moaned softly, her breathing heavier as I continued my descent. 

“You don’t need to ask permission to cum tonight baby girl,” I explained.  
She nodded, watching as I placed soft kisses across her thighs. I took the end of one of the bows of her panties between my teeth and pulled it open. Roxy bit her lip again as I moved onto repeat the same action on the other bow. I pulled her panties off, they were well and truly soaked. I kissed my way around her entrance, her legs spreading a little further in the hopes I would stop teasing her. My own eagerness had gotten the better of me and I leaned in further to finally taste her. She moaned as I traced her clit with my tongue, her hips bucking a little. I knew it wouldn’t take her long to cum with the state I’d left her in at the restaurant. 

I hoisted her legs over my shoulders for a better angle as I continued to taste her. Roxy continued to moan, her fingers tangling in my hair and tugging gently. I slipped two fingers into her, curling them against her sweet spot which quickly turned her into a moaning, panting, writhing mess. I’m surprised she’d even lasted this long. With a cry of my name Roxy reached her first climax of the evening, her back arching off the bed. I continued to work her through it until overstimulation set in and she winced. I sucked my fingers clean before kissing my way back up to her lips. 

I reached across to the bedside table drawers and felt around blindly until I found a condom. I tore open the packet and put it on before kissing Roxy once more. She wrapped her arms around me and I slowly pushed into her. Roxy moaned, her nails digging into my shoulders. I wanted to make every part of her mine. But where was the fun in doing everything in one night? Right now, we both just needed to fuck each other. We’d both waited long enough. Roxy wrapped her legs around my waist, forcing me deeper as I began to speed the pace up. I took hold of her wrists and pinned them either side of her head, forcing a louder moan from her. 

 

I guess that came in to her wanting to give me complete and utter control, which again we would explore more later. Besides we needed to have a proper discussion about what she would and wouldn’t allow me to do to her. I groaned against her neck before deciding to change things up a little. I let go of her wrists only to take hold of her ankles and hoist her legs up so her ankles were resting against my shoulders. With the change of position and pace Roxy seemed to get even louder, throwing her head back against the pillow and screwing her eyes shut in pure pleasure. 

The room was filled with the sound of skin against skin and our various moans and curses. I could feel myself getting close. I forced it to the back of my mind and focused on Roxy. I released one ankle and reached between us, rubbing her clit. She moaned my name and whined various curse words. Finally, she reached her second climax, crying out my name again as her legs shook a little. She fisted the sheets beside her as I kept the pace up. I reached my own climax, groaning her name. I placed her legs back down either side of me before slowly pulling out. I disposed of the condom before getting into bed with her.   
She was still breathing heavily, looking thoroughly fucked out. I pulled her into my arms and kissed the top of her head.   
“Sleep baby girl. We can play more tomorrow.


	7. Chapter 7

Chapter 7

Roxy’s P.O.V

I awoke in the morning and rolled over to snuggle into Negan, however his side of the bed was empty. I frowned and sat up, scanning the room. I listened carefully to hear and smell breakfast being cooked. I had no clothes to wear for today, this was going to be a problem. Not so much if he expected me to go straight home but he had said we would ‘play’ more today so I think he intended me to either stay another night or at least to the end of today. I forced myself out of the comfortable bed and picked up his shirt from last night. I put it on and closed a few buttons. 

I headed out into the kitchen to find him as I had suspected. He was cooking breakfast, dressed in a simple pair of jeans and white t-shirt. It was odd to see him in something other than a well-tailored suit. But he was just as attractive in casual clothing. He glanced up from the pan on the stove and smiled at me.   
“Morning baby girl,” he greeted cheerily.   
“Morning.”  
His eyes travelled across my body, smiling at my choice of clothing. 

“You hungry?” He asked, a mischievous glint in his eyes.   
“Starving,” I played along.   
“Good.”  
He finished up breakfast and plated the omelettes up. We sat together at the breakfast bar and I took a bite of the food. Good in bed, good in the kitchen…how did I get so lucky? Even if we weren’t officially dating. It was just sex.   
“So, I was thinking perhaps we could get you some new clothes today, gives me a chance to spoil you some more,” he spoke.  
So, he wanted me to stay longer than I had anticipated, I was fine with that. 

“I don’t have anything to wear and I can’t exactly walk around outside in just this,” I replied.  
“As nice as this sight is your right. I think I’ve got some things around that should fit you.”  
That hurdle had now been crossed. Until my brain began over thinking. He had other woman’s clothes? Was he sleeping with someone else as well as me? I don’t think that’s something I wanted to get myself into. I’d be constantly thinking that I was good enough. As if reading my thoughts, he placed his hand on my knee.  
“It’s just from old sugar babies ok. Stuff they left behind, nothing to worry about,” he reassured. 

My curiosity had picked up, it was obvious I wasn’t his first and I probably wouldn’t be the last. But I needed to know more, needed to know the fine print.   
“How many have there been before me?” I asked.  
“Eight, although one of them technically doesn’t count as a sugar baby. Him and I sort of just came to a mutual agreement.”  
I almost spat out my orange juice, “him?”  
“Yeah. You’ll probably meet Simon soon enough.”  
“Ok now I’m really interested, has he been the only guy?” 

Negan chuckled, shaking his head, “no he hasn’t. There’s been two others, Rick and Daryl. Rick was a sweet guy and Daryl just liked to be a handful.”  
“Do you still keep in contact with some of them?”   
“Yeah, Frankie is my hair dresser and masseuse. Simon and I see each other at least once I month when there’s an event on at the club.”  
“Club?”  
“He owns a fetish club.”  
Again, I almost choked on my juice. Perhaps I just should stop eating and drinking whilst this conversation continued. 

“Is that something you would be interested in?” Negan asked me.  
I had never really thought about it. I mean there was no harm in trying it at least once. If I didn’t like it then I wouldn’t go again.   
“I’m curious about it, so I would like to go with you,” I replied.  
“Good. I can’t wait to show you off baby girl.”  
I bit my lip at this and the fact his hand was slowly traveling up my thigh.   
“Everyone in the room will now that your mine and they can’t touch you. Something tells me you like being the centre of attention,” he continued.  
The thought of being shown off to other people that desired me just as much as he did, did sound appealing. 

His hand stopped on my thigh and I let out a deep exhale to calm myself and the pulse between my legs.   
“There’s an event coming up next Saturday. You can come to mine in the morning and then we’ll head down together,” Negan explained.  
“Will I have to wear anything special?”  
“I’ll have that covered, don’t you worry.”  
I couldn’t help but worry, the things that came to mind for fetish club and clothing were full body gimp suits and everything was leather, latex or PVC, which didn’t seem comfortable. Although the thought of Negan in something leather was appealing. 

“You promise it won’t be something too out there?” I asked.  
“Baby girl it’s your first time doing shit like this, I wouldn’t expect you to walk around in hardly anything. I was just going to start you off with something simple. Just like last night, we started off simple as much as I wanted to spank that perfect ass of yours.”  
I bit my lip again, he could spank me now if he wanted. I definitely wouldn’t have been opposed to it last night but I did appreciate that fact he wanted to take his time with me. I’m sure if he threw me in the deep end it would have scared me off. 

We finished up breakfast and decided it would be best to take a shower. Although I’m sure he didn’t just want to clean up in the shower. I followed him into the bathroom. Negan turned on the water, letting it heat up a little before undressing himself. I took off his shirt and stepped under the warm spray of water. He joined me, wrapping his arms around me and kissing the back of my neck. I smiled to myself, pressing myself back against him. I could feel how hard he was already. I turned to face him, kissing him. I wrapped my arms around him, wanting to be as close as I could to him. 

He pushed me against the wet tiles, picking me up and wrapping my legs around his waist.   
“You wore my shirt on purpose, didn’t you?” He asked.  
“I have no idea what you mean,” I spoke, playing innocent.   
“I was half tempted to have you over the kitchen counter, you would have liked that wouldn’t you? Me forcing you over the nearest surface and having my way with you.”  
“I’d like you to have your way with me now.”  
“I’m really going to have to teach you patience, baby girl.”  
Negan pushed into me, both of us moaning at the contact. I closed my eyes, my head thrown back against the tiles. 

He kissed and nipped at my neck as he began a fast pace, using the wall as leverage to hold me up. Negan gripping my hips, pulling me down on to him so that I met him with each thrust. God, I don’t think I could ever get bored of sex with him. He could fuck me all day long if he really wanted and I would have no complaints. One hand fisted into his hair whilst my other hand clutched the back of his neck, my nails digging into his skin. His lips moved down from my neck to my chest, leaving more possessive marks across my pale skin. I moaned as he reached my breasts, arching into him. A warmth had worked its way into my belly meaning my orgasm was near. 

I knew this would be over sooner than I would have liked. But it’s not like I wouldn’t have any more opportunities to fuck him. Negan groaned against my skin, continuing to bring me to closer to the edge.   
“Fuck, I can’t get enough of you baby girl,” he groaned.  
I could only moan his name in response, the sound of our moans and groans echoing in the shower. Thank god, he lived alone. he reached between us, finding my clit and rubbing it with his thumb. I felt my stomach do a loop as the pleasure increased and almost became too much.   
“You gonna cum for me baby girl?” He asked.  
“Yes daddy.”

As if on cue I reached my climax, my body going completely stiff as I cried out his name over and over. Negan reached his own after a few more thrusts, letting out a loud curse as my tightness continued to milk his cock. He gently set me down on the floor as I continued to cling to him as my legs were shaky. Eventually my muscles regained control and I could stand on my own. We cleaned ourselves up before stepping out the shower. I dried myself off before wrapping the towel around my body. Negan dried and led me back into the bedroom where he found me some clean clothes I could change into. It was a simple pair of black jeans, plain t-shirt and a red jumper. At least I would be warm.

He changed into another clean pair of jeans, t – shirt and leather jacket. If I hadn’t just cleaned myself up I would have probably jumped on him. Instead we headed further into the house until he opened a door to a garage. I should have expected to him have more than one vehicle. There were two more cars and a classic Harley Davidson. He really was full of surprises. He handed me a helmet before putting on his own. He climbed on the bike and started the engine. The garage door opened at the touch of a button and I put my helmet on. I climbed onto the back of the bike, wrapping my arms around his waist and holding on tight. 

Negan got us to our destination quickly and safely, parking the bike and pushing down the kickstand. I climbed off the bike and put my helmet away in the back compartment that was just big enough to fit two. I glanced around at the strip of stores, of course they were all top fashion brands meaning the clothes would be nice but the price tag wouldn’t be. Negan led me inside a Versace store and I felt so out of place. Even the shop assistants looked like models. Negan was already looking around the store and picking things out for me to try on.   
“Please don’t pick out too much,” I spoke.  
“Baby girl, if I want to spoil you then I’m going too. Besides you need some new work clothes as well as casual wear and I’m sure you could do with some nice dresses too. You’re going to need something nice to wear if I keep taking you out.”

Negan had worked his way around the store and then handed me the clothes to go and try on. There were ten items in total. I grabbed the price tag of a white pencil dress and my eyes widened at the price. He must be mad. I forced myself into the dress and looked at myself in the mirror. This would be really nice for work and I did look pretty good in it. I sighed and headed out of the changing cubicle so he could see how it looked himself.   
“You wanna be fucking careful wearing that around me at work,” he spoke.   
“You wanna learn to control yourself,” I replied.   
I retreated backwards before he could say anything else. I tried on the rest of the clothes, giving in and putting the prices to the back of my mind. It was surprising how good his taste was and that he’d picked out my size perfectly. 

I had at least two normal every day outfits, two work outfits and two evening dresses. Negan took the clothes from me and paid for them before handing me the shopping bag. He then dragged me to a shoe store and brought me two pairs of heels, some pumps and a pair of trainers. Maybe I could get used to this after all. Providing he let me spoil him back…in other ways.


	8. Chapter 8

Chapter 8

Negan’s P.O.V

Unfortunately, Roxy and I didn’t have much time together during the week as we were both super busy. Thankfully with how busy we were the weekend came quicker. Roxy arrived at mine around 11am. This time she had brought an overnight bag with her. We had lunch around 12, sitting down in the lounge together.   
“So, when do I get to see my outfit for tonight?” Roxy asked.  
“Why? Your still worried I picked out something that barely covers you?”  
“A little.”  
I smiled and led her into the bedroom, opening up the wardrobe. I had her outfit hung up ready and waiting for her.

I produced the black latex dress and showed it to her. The dress itself was tight fitting and long enough to just about cover her ass, the sleeves puffed out at the ends only attached to the dress by buckles. This went for the collar piece as well. She could wear it some stockings and heels. She looked it over looking curious.  
“Is it as bad as you thought?” I asked.  
“No. It’s actually quite nice. What are you going to wear?”  
“My jacket, maybe some more leather. But there’s something else I want you to wear for me tonight.”  
“Ok?”

I produced the medium sized pink glass butt plug that had a diamond embedded into the base. Roxy stared at it for a moment, not too sure how to respond. Eventually she shrugged.   
“Alright,” she spoke.   
“Daddy needs to claim all of you baby girl,” I replied.  
Roxy bit my lip at that, my gaze turning predatory. Her cheeks flushed a little.   
“On your hands and knees for me baby girl,” I instructed.  
She did as she was told, climbing into the centre of the bed on all fours. I followed her, kneeling beside her on the bed. 

I pulled her jeans and panties down so they were bunched around her knees. I just had to take this slow and gentle. I opened up the bedside drawer and produced a bottle of lube, popping the cap and applying it to my fingers first. I pressed a single wet finger to her hole, circling the tight ring of muscle. After applying the nessacary lube I slowly pushed the digit inside. Roxy did her best not to tense at the foreign feeling. I continued to take it slow, not moving until I knew she was ready.  
“Your doing so good baby girl,” I praised.

I began to work her open, feeling her slowly loosen around my finger. Eventually I pressed a second finger into her, continuing to loosen her up. I started a scissoring motion and she took a deep breath at the slight discomfort.   
“Breathe for me baby girl. Your taking this like a champ,” I continued.   
Roxy did as she was told, closing her eyes and focusing on breathing in and out. Satisfied with my motions I removed my fingers. I applied some more lube to the plug before slowly pushing it inside. Roxy grasped the bed sheets, her head falling forward as she exhaled deeply. 

I squeezed her rear before going to the bathroom to wash my hands. I returned a few second later, admiring the sight before me. She looked so good like this, it was half tempting to fuck her now. But I had to wait for later. That didn’t mean we couldn’t do other things however.   
“You know what would look even better right now baby girl?” I spoke.  
“What, daddy?” She asked, looking round at me.  
“If you ass was covered in my handprints.”  
She bit her lip, the look on her face telling me she wanted it. Good girl. I stepped closer to the bed, grabbing her hips and pulling her closer. 

“I’m not going to spank directly over the plug ok baby girl. I think ten should be enough, don’t you?” I reassured her.   
“Yes, daddy.”  
I brought my hand down on her rear, the harsh smacking sound filling the room. Roxy gasped, her back arching a little. I brought my hand down on the other cheek, spreading the pain. Eight more. The next three came in quick succession, the redness starting to blossom against her pale skin. I smiled to myself, rubbing over her skin to soothe the sting. She pressed herself against me, probably wanting me to touch her somewhere else. 

“Halfway there. How you doing, baby girl?” I asked.  
“I’m ok, daddy,” her breathing was heavier.   
I brought my hand down again, giving her another moment to let the sting slowly turn to a soft tingle. The last four came in quick succession again, earning a soft whine from her. I looked down at my handiwork, her ass red with the shape of my hand. I leaned down and kissed over the redness. My cock was pressing against my jeans almost painfully. I pulled Roxy’s panties and jeans back up before she turned around to face me. She glanced down, noticing how hard I was. She instinctively licked her lips before meeting my gaze. 

“Daddy?” She asked.  
“Yes, baby girl?” I replied.  
“Can I suck your cock please?”  
I smiled, “because you asked so nicely.”  
She returned the smile and hopped off the bed. I sat down on the edge, letting her kneel between my legs. 

She undid my belt and loosened my jeans, slipping her hand inside. I lifted my hips so that she could pull my jeans and boxers down. My cock sprung free, precome already leaking from the tip. Roxy placed a soft kiss to the head, kissing her way down to the base. I bit my lip, she wasn’t allowed to tease. I tangled my fingers in her hair and guided her back to the head of my cock. She opened her mouth, taking me into her mouth. I groaned, forcing her to take as much as she could. I hit the back of her throat and I felt her gag around the head. 

I watched as her eyes welled up with tears and pulled her back by her hair, she started sucking on the head for now. I groaned, my hips bucking a little. Her tongue traced figures of eight on the sensitive tip, occasionally dipping in to the slit. Fuck. If I’d known she was this good at giving head I would have let her suck my cock a long time ago.   
“Fuck, that’s it baby girl,” I praised.  
Roxy began to take more and more of me in her mouth, hollowing her cheeks. My grip on her hair got tighter and my moans got louder. She looked up at me through half lidded eyes, continuing the pace. I bit down on my bottom lip, my hips bucking again. 

I began using her hair to guide her and set the pace I wanted. Roxy reached up and began to use her hand for what she couldn’t take in her mouth. We’d have to work on that, I wanted her to be able to take all of me in her mouth.   
“Maybe I should fuck your mouth all damn day because you just keep getting better baby girl.”  
My cock hit the back of her throat again and I held her there for a little while, making her gag and her eyes water once more. Finally, I released her enjoying the sight of her cheeks flushed, her eyes watering and my cock between her lips. 

“Baby girl you look so good with my cock in your mouth.”  
At this point I started fucking her face, chasing my oncoming orgasm. Roxy let me use her for my own pleasure. My hips finally stilled as I shot my load down her throat with a loud ‘fuck’.   
“Swallow,” I ordered.  
Roxy did as she was told, swallowing my cum. I cupped her face, smiling down at her.   
“Hey baby girl, how about a thank you,” I smirked.  
“Thank you daddy.”  
“Such a fucking good girl for me. You fucking wait for tonight. I’m gonna reward the shit out of you.”


	9. Chapter 9

Chapter 9

Roxy’s P.O.V

Negan parked the car in a nearby lot and we walked the rest of the way to the club, it only took us two minutes. He had given me a large coat to wear over my dress whilst we were in public. He hadn’t bothered with one however, looking semi normal in all leather. We headed inside the building and Negan handed over the tickets at the front desk. Negan helped me out of my coat and that was taken to the cloakrooms. I took a deep breath to prepare myself. There wasn’t any backing out of this now. Negan laced his fingers with mine and led me inside the main room. it was already half filled with people dressed in all types of clothes. Some were wearing full body fetish suits; some people were wearing just underwear. I spotted a girl wearing a beautiful black and white latex cape, she was stood beside what I guessed was her sub. 

My outfit wasn’t so bad after all, not now I’d seen some people in the bare minimum. Negan led me over to a male dressed in a leather cop uniform, with a huge handlebar moustache. I had to hold back from giggling, he looked like a member of The Village People. Negan and the man embraced, smiling at each other. This must be Simon.   
“Glad you could make it,” Simon spoke to him.   
“I’m sorry I couldn’t make the last one. This is Roxy,” he introduced me.  
Simon turned his attention to me, looking me up and down before taking my hand in his and kissing it.   
“He mentioned you were beautiful, I think that’s an understatement,” Simon spoke.   
I felt a blush creep up on my cheeks. Negan had been telling people about me? 

“So, this your first time?” Simon asked me.  
“Yeah.”  
“Well the first time is always the most nerve wracking but I can assure you that you’re in safe hands. Not just with him but with me too. Has he explained how these things work?”  
“No. He’s kinda just thrown an outfit at me and that’s it.”  
Simon laughed, rolling his eyes. Negan had gone off to the bar area to get us some drinks.   
“Of course, he has. So, there will be a bunch of workshops on this floor it’s up to you if you want to try it out, if your too shy that’s fine you can just watch. Upstairs is the more hardcore shit, again completely up to you what you do. And downstairs are the private rooms, up to six people can go in a room at a time,” Simon explained.

Ok now this was a lot to process. What the hell did he mean by the more hardcore stuff? Did I even really want to know? Negan came back over, handing me a cocktail. I could definitely use the liquid courage right now. Simon left us to go check on a few things. Negan took in my expression and raised an eyebrow.   
“What does he mean by the more hardcore stuff?” I asked, my curiosity getting the better of me.  
“You mean upstairs? That’s medical play. I’m not into that so you don’t need to worry about that floor ok.”  
I breathed a sigh of relief. Thank god for that, medical play didn’t exactly sound pleasurable in any way. 

Negan and I remained where we were, taking sips from our glasses. I guess I would be following his lead for most of the evening.   
“Simon mention what goes on down stairs?” He asked.  
“He told me how many people can go in at a time. I’m guessing they’re used for sex.”  
“Yeah. Is that something you’d be interested in?”  
“Perhaps not with four other people. Just you and I. Orgies aren’t something that interests me.”  
“What about sharing?”   
“Sharing?” 

“I watch as someone else fucks you, or vice versa,” he explained.  
I turned my nose up, no way was I watching as he fucks someone else. My expression gave him the answer he needed and he nodded understandingly.   
“That’s fine. I’m not up for sharing you with anybody else. I just didn’t know if it was something you were into,” he continued.  
“I enjoy the intimacy of being just yours. Someone else wouldn’t feel right.”  
“Im glad you feel that way baby girl because there’s no way in hell another person is going to touch you whilst you belong to me.”

There came that possessiveness again. I liked it when he got like this. It was nice to feel so wanted. We finished our drinks and made our way around this floor, exploring different workshops. First was a simple spanking/whipping station. Various people having various tools used on them. Paddles, whips, hands, riding crops, canes and belts. The last two seemed like the most painful. I liked the idea of the riding crop though. Negan noticed my interest.  
“You wanna give it a try baby girl or is your ass still sore from earlier?” He asked.  
“It’s still a little sore, sorry daddy.”  
“Nothing to be sorry about. I've got a crop at home.”

“Promise you'll never use a cane or belt on me,” I spoke.  
Negan chuckled, “baby girl those aren’t the worst things. That’s saved for the top floor.”  
“What could be worse than those?”  
“Gloves that have little pins on the palm.”  
Oh God, that really was worse. I shuddered at the thought of how painful that must be, yet there were people out there who were into it and who was I to judge? Negan and I moved on to the next workshop. Bondage. Particularly with ropes. This also caught my attention. Some of the designs were oddly pretty. The knots looked difficult though. 

I watched as one woman was suspended by the ropes. I bit my lip, imagining myself in her place. All tied up and helpless. Negan could do whatever he wanted to me. Well he could anyway but with the ropes I would be unable to stop him or resist. It did play into my fantasy of letting him have complete control. Having him force himself on me whether I wanted it or not.   
“Do you know how to do knots like that”? I asked.  
“I know a few. But I can learn more.”

Negan took me over to a small table, which was selling various items. He picked up a leash that would attach to the collar of my dress. I bit my lip, feeling the heat rush to my cheeks once more. I shouldn’t be so embarrassed when there were people fucking downstairs. I guess I'd just been so used to sex being a taboo subject and the kinkier things something to be embarrassed about. Everyone else was comfortable enough to show everyone their kinks so I should be too.

Negan paid for the leash and attached the clip to the metal ring on my collar. He put his hand through the loop and gave it a quick tug to test its strength. Satisfied we continued through the first floor. We got some more drinks and found a comfy spot to sit down. He forced me on to his lap, his hand on my knee. I kissed his neck, making my way up to his lips.   
“Careful baby girl we might gain an audience,” he spoke, his voice dangerously low.  
I glanced over my shoulder, scanning the crowd. A few people were looking in our direction but I couldn’t be sure if they were looking directly at us.

I turned back to Negan, kissing him again, “there are couples doing worse than us out in the open.”  
“True. And we can always take this elsewhere of you wanted.”  
“Can we look around a little more first?” I asked.  
“Of course, we can.”  
I climbed off his lap and we continued looking around this floor. I stopped to gawk at a stall that was selling latex and PVC clothing. I guess I wanted something else than just this dress.   
“Not to put you off baby girl but there’s much nicer stuff online. It’s where I got your dress,” Negan spoke.

Daddy knew best. Eventually we'd done a complete circle of the first floor, going back to the bondage workshop for another quick look. Negan could see my interest and suggested I try it but I was still to shy. Maybe next time. Thankfully he didn’t push me. My curiosity was growing about the other two floors but I could save the top floor for when I was feeling a lot braver. We could try the bottom floor though. Negan led me downstairs to the bottom floor. There was a long hallway, various doors leading to various rooms. 

Negan found a room near the end of the hall that had a vacant sign on the door. He opened the door and let me go inside first. Well this wasn't what I'd expected at all. The room was well lit, a panel on the wall to control the lights. Negan followed me inside after changing the sign on the door to occupied. He locked it as well, just in case. There was a bed in the centre of the room, complete with clean sheets. I’d expected this place to look more like a back alley than a hotel room. 

There was a box of goodies too. Negan looked through it, finding what he wanted and making sure it was clean before showing it to me. He'd found rope.   
“Strip for me baby girl,” he spoke.   
I did as I was told, slowly and carefully taking it off. I unlaced my knee-high boots and took them off as well as my stockings. Negan came over to me and pulled my wrists together before tying them tight. He helped me on to the bed, making me kneel before taking my bound wrists and lifting them over my head, securing the rope to a discrete celling hook. I was forced to change position a little, going up higher on my knees, my legs apart. 

Negan admired his handiwork before removing his own clothes. He circled the bed, disappearing behind me. I felt the bed shift under his weight as he climbed on, still behind me. Negan placed his hands on my hips, his touch barely there. I shivered, unable to do anything but wait. Negans fingers travelled up my sides and round to my chest, cupping my breasts. I arched into his touch, the anticipation building in my stomach making me feel giddy. Negan pressed himself against me, his hard cock pressed against my rear. I pressed back against him, hoping that with enough friction he would give me what I wanted. 

He chuckled, one arm locking around my waist to hold me in place as he continued to play with my breasts.   
“Not yet baby girl, I told you I’d teach you how to be patient,” he spoke.  
I whined. The hand playing with my breasts moved down lower until he reached between my legs, thumbing at my clit. I gasped, the pleasurable sensation leaving as quickly as it had come. His fingers went back to ghosting over my folds. I strained against the rope, needing so much more of him.   
“So wet for me already,” he said more to himself.   
My chest heaved as I was slowly being driven mad by the feather light touches. 

Negan took his hands away and began to change position, his head appearing between my legs. I was just out of reach from his mouth. I strained against the rope once more, desperately trying to lower myself on to his tongue. He smirked, taking hold of my hips and swiping his tongue across my entrance. I bit my lip, focusing on keeping my breathing even. He was only using the tip of his tongue, teasing me further. I arched and writhed trying to find the perfect position. Negan dug his fingers in as a signal for me to keep still as he continued teasing my clit with the tip of his tongue. 

“Daddy p-please,” I managed, my voice a pathetic whine.   
“What is it baby girl? You need to tell daddy what you want.”  
“Please don’t tease me anymore. I need you.”  
“How badly?”  
“So, fucking badly.”  
Negan licked over my clit, tracing various patterns against it and giving me the friction I needed. I moaned, my eyes closing instinctively. I couldn’t help but rut against him, continuing to strain against the rope. I’m surprised the hook hadn’t given way yet.

Negan continued eating me out for a little while before deciding I’d had enough. I whined at the loss of contact, having had my orgasm creeping closer. He changed his position again so he was laying further across the bed and my legs were either side of his waist. I was hovering just above his cock, the tip pressing against me but I wasn’t low enough to sink down onto him. I was starting to become frustrated, needing all he could give me. Negan’s hands went to my hips again and he slowly pushed into me. I cursed, my hips bucking against his. 

This position was going to provide a little more effort from both of us but I didn’t care at this point. Negan gripped my hips as he continued to thrust up into me, his pace getting faster. I positioned my hips in a way to make it easier for him, wishing I could be untied and ride him, taking all the pleasure he could give me. My arms were starting to ache but for now the feeling was semi ignorable. I felt the hook start to give until my weight tore it from the ceiling. I collapsed on Negan unable to break my fall with my wrists bound. He caught me and started to laugh.   
“You ok?” He asked, still chuckling. 

“My arms hurt a little. What about you? I didn’t elbow you somewhere painful?”   
“I’m fine baby girl.”  
We both laughed at the silliness of the situation before finally he untied my wrists. I leaned down to kiss him softly.   
“Perhaps we should try a different position next time,” I suggested.  
“Or Simon needs to get these things installed properly.”  
He craned his neck so he could kiss me again, his fingers in my hair. It felt nice that even with this purely sexual relationship we were able to still laugh at ourselves when it came to things like this. We weren’t taking each other too seriously. It was a thing normal couples did. 

Now that my wrists were free however, I’d be able to take what I wanted. I straddled him and slowly sunk down onto his cock, moaning at the feeling. I clung to his shoulders to keep myself steady as I started to ride him. Negan matched my pace, the sound of skin against skin and our moans slowly filling the room. I rolled my hips against his, earning a loud groan from him, his head thrown back against the sheets.   
“You look so fucking good riding my cock like this baby girl,” he breathed.   
I could only moan in response as my orgasm began to build again, that being the only thing I could focus on. 

Negan could tell I was close and reached between us, rubbing my clit in time with his thrusts.   
“You gonna cum for me baby girl?” He asked.  
“Yes daddy,” I replied.   
A few more strokes and I reached my climax, crying out his name my hips bucking against his as wave after wave hit me. Negan cursed, his fingers digging into my flesh as he reached his own moments later. I rested on top of him as he wrapped his arms around me and kissed my temple. We stayed like this for a while, just holding each other as we came down from our highs. 

“So, when’s the next time we can come back?” I asked.  
“Here? There’s an event once a month. I’m glad to know you wanna come back though.”  
“Maybe next time I’ll be brave enough to try out some of the workshops.”  
“Maybe. If I give you the chance what with next month’s theme.”  
“Oh?”  
“Heaven and hell. It’s a bit cheesy I know but the thought of you in some white underwear and pretty angel wings makes it something to look forward too.”  
I smiled and leaned down to kiss him again. We decided we should probably head back to his place. 

I climbed off him and redressed myself. Negan put his own clothes back on and we made sure the room was clean and tidy before we left. Simon caught us as we were leaving, holding a shot of tequila.   
“You two going already?” He asked.  
“Afraid so,” Negan answered.  
“Well, did you have a good time Roxy? That’s the main thing,” Simon turned his attention to me.   
“It was interesting and I’ll be happy to come back next month.”  
He smiled, “great. Glad to hear it. Don’t let him wear you out too much now.”  
I blushed and held back a laugh, he’d already done that.


	10. Chapter 10

**Notes for the Chapter:**

> WARNING: This chapter contains a discussion about a rape kink/fantasy. Dont like, dont read. The last thing I want to do is trigger or upset someone with this.

Chapter 10

Negan’s P.O.V

I awoke a little past 7am, glancing over at Roxy who was still asleep beside me. I carefully got out of bed and changed into some casual wear before heading to the kitchen to make her breakfast. I’d let her sleep in, after the night she had she deserved it. I was happy she had taken the club so well. I didn’t take many of my sugar babies there. Only two others had been besides her. I decided to make breakfast muffins, getting to work on beating the eggs. I was excited to take Roxy again, excited to see if she would try out any of the stations the next time. 

Half an hour later Roxy padded into the kitchen, wearing nothing but one of my shirts. She hoisted herself onto the kitchen worktop, her legs dangling over the side. I had half a mind to spank her over it but I’d give her some time to wake up first. She smiled softly, making a sound of contentment at the smell of cooking.   
“Morning daddy,” she spoke cheerily.   
“Morning baby girl. You sleep well?” I asked.  
“Like a baby.”

I headed over to her and kissed her softly.   
“What would you like to do today?” I asked.  
“Whatever you want.”  
“No. Because you were so good last night, I want to know what you want to do.”  
“I don’t know. Maybe watch a movie or something? Or is that too domestic for you?” She joked.  
“I can do domestic. I can be more domestic than a movie too.”  
“Well then what would you suggest?” She placed her hands on her hips.  
“I’d like to take you out for the day and spoil you again but like I said it’s up to you.”

Roxy considered it for a moment, “that sounds fine. Just some of my muscles are a little achy from last night.”  
“I can book us in for a couple’s massage. I know a girl.”  
“When you say you know a girl…have you…”  
“Slept with her? Tanya used to be one of my sugar babies but she met someone else, someone to be in a proper relationship with. You have nothing to worry about.”  
Roxy still didn’t seem comfortable with the idea, her arms now folded across her chest. I placed my hands on her hips, pulling her closer.

“Or I could give you a massage instead? Would you prefer that?” I asked.  
She smiled softly and nodded. I kissed her cheek and checked on breakfast. I plated up the muffins and Roxy jumped down from the counter, sitting on one of the bar stools instead. We ate breakfast before moving back to the bedroom where I could give her a massage. She took off my shirt and laid on her front on the bed. I knelt on the side of the bed and began rubbing her shoulders, moving down to her back and hips. She made a sound of contentment, her muscles relaxing under my touch. I continued my journey south, reaching the backs of her thighs and legs, earning a soft moan from her. 

I smirked, “you sure it wasn’t because you wanted my hands all over you baby girl?”   
I heard her giggle, “it wasn’t originally.”  
I finished with her feet and she rolled over on to her back, looking completely relaxed and even a little sleepy. I headed to the bathroom, taking a quick shower before changing into clean clothes. Roxy was fully dressed in clothes that I had brought for her. I smiled and kissed her softly.   
“So, you wanna go out or stay in? We can order takeout for lunch,” I asked.  
“I’m honestly happy enough to stay in, you don’t need to buy me things all the time.”  
“Alright baby girl.”

We headed into the living room where Roxy headed over to the DVD cabinet and began searching through the titles.   
“I’m half expecting to find a bunch of erotic movies in here,” she joked.  
“Fifty Shades of shit? Fuck no. Baby girl your smart enough to know that isn’t a realistic or healthy BDSM relationship.”  
“I didn’t mean that one in particular but I do agree with you. The movies and the books are a mess.”  
“I have Netflix if you can’t find anything.”  
“I’ve found a few things. Just trying to decide.”

Roxy picked out her various choices and put them on the coffee table. Basic Instinct, Clue and Mulholland Drive. I picked up Mulholland Drive and raised an eyebrow.  
“You seen this before?” I asked.  
“Nope.  
“You’re in for one hell of a mind fuck.”  
“I didn’t think you’d have the special edition of Clue though, all three endings.”  
“Can’t beat a good Tim Curry movie.”  
“True.”  
We decided on Mulholland Drive first, get the mind fuckery of David Lynch out the way first. 

I kept glancing at her for certain scenes so I could see her reactions. Needless to say, by the end of the movie she looked very confused.   
“What the fuck? I’m so fucking confused. So, Diane and Betty are the same person or…am I missing the point?” She asked, hoping I would be able to give her answers.  
“Doppelgangers.”  
“And that ending?”   
“I have no fucking idea.”  
She laughed at this, “well that makes two of us. What’s for lunch?”

“Chinese?”  
“Sounds good.”  
We ordered plenty of food to last the both of us probably until tomorrow. It arrived within the hour and we started the next movie, deciding on Clue whilst we ate. Once we were both pretty full I pulled her into my arms, her head resting on my shoulder. I smiled to myself, kissing the top of her head. This was nice. But unusual. Most of the sugar babies I’d had jumped at the chance for me to spoil them. They would choose a shopping spree over a movie marathon any day. This was nice for a change, not that I minded spending my money. I was going to make sure Roxy got plenty of money for last night. Now would be a good time to discuss her sexual preferences further. 

“So next time we go to the fetish club you willing to wear a little less than last time?” I asked.  
“How little are we talking?”  
“Bra, panties, stockings.”  
“I can do that. I was worrying you’d have me walk around in a thong and nipple pasties or flat out naked.”  
“Bra and panties will be about as naked as you get in the eyes of other people.”  
“Good to know.”  
“Is there anything else you want to try that I’m not aware of? Anything you’ve heard of but been too scared to try with other people?”  
Roxy nibbled on her bottom lip, avoiding my gaze clearly ashamed of what had just come to mind. 

“What is it baby girl? I’m not going to laugh at you if that’s what you’re scared of,” I explained.  
“I’m not scared that you’ll laugh at me. I’m scared you’ll be creeped out.”  
“Well as long as it doesn’t involve piss or shit or animals.”  
“When I said I wanted you to have complete control…I kinda meant that I wanted you to force yourself on me even if I said no.”  
Roxy hid her face with her hands, afraid of my reaction. I took her hands away from her face and kissed her knuckles.  
“A rape fantasy?”   
“Don’t call it that, it just makes it sound worse. I mean half of me is like, why would you even want something like that, that’s fucked up. I never even considered it until we started this.”

“You trust me that much?” I asked.  
“Yes. I wouldn’t imagine doing something like this with anybody else. And part of the fantasy is that I start to enjoy it anyway.”  
“But initially you’re going to be saying no and trying to fight me?”   
“Yes.”  
“This is going to be some kinkier roleplay,” I said, trying to make her feel better about it.  
“I completely understand if it’s something you’re not comfortable with.”  
“I need to think about it. You understand that a lot of planning would need to go into this scenario. We’d need to develop a safe word just in case I really do something wrong and you need me to stop.”

“But you’re not saying no to the idea?”  
“I’m not saying yes right now either. There are other things I want to do with you before we go further into the deep end.”  
“Ok. Thank you for this.”  
“You don’t need to thank me. You should be comfortable to talk about sex with me, well women should be comfortable to talk about sex regardless. It’s a darker kink but between two consenting adults who trust each other there shouldn’t be a problem with it. It’s nothing to do with anybody else, just you and I.”  
“If only everybody could have your outlook.”  
I kissed her softly to stop her from worrying about the situation. 

“You just like the idea of me finding you that irresistible that I have to have you no matter what,” I explained.  
“That’s part of it, yeah.”  
“Anything else you wanted to try?”  
“That’s the thing I’m most embarrassed about if that’s what you mean.”  
I kissed her cheek, using kisses to reassure her. We finished Clue and finished off the day with Basic Instinct. We finished off our Chinese leftovers before Roxy decided to head home so she could get enough for sleep before work tomorrow. 

I kissed her goodbye, watching as she got into her car and drove away. I sighed, missing her company already even if I would see her in ten or so hours. I cleaned up the takeaway wrappers and put the DVD’s back in the cabinet. I headed to bed after an hour, the sooner I got to sleep the sooner it would be tomorrow and the sooner I would be able to see her again.


	11. Chapter 11

Chapter 11

Roxy’s P.O.V

I headed into the office, wearing a new white pencil dress. I’m sure Negan would appreciate me using his money to buy myself nice clothes. I’d curled my hair and made sure to wear it down and put on a new deep red lipstick. Dwight looked up from his booth and smiled.  
“Who’s the lucky guy?” He asked.  
“Not you,” I smirked.  
Dwight returned the smirk and went back to typing. I sat down in my booth and booted up my computer. The office had a chat system, which was useful if you needed to send something across or were bored. The chat window popped up in the corner with a soft ding, telling me I had a new message. 

I glanced over my shoulder to make sure nobody was looking at my screen before looking at the message. Of course, it was from Negan.  
_Come to my office. Now._ The message read. I couldn’t tell if I was in trouble or not. I locked my screen so nobody could see anything and headed off to his office. I knocked first and waited to be called inside. I closed and locked the door behind me, just in case. Negan was dressed in another fancy suit, the jacket draped over the back of his chair and his red tie a little loose as if he were stressed already. Negan glanced at me before looking back down at the paperwork spread across his desk. 

“Everything ok?” I asked.  
“Just wanted to see you before I get to tied up,” he replied.  
I couldn’t help but smile at that. It was nice to hear, even if this wasn’t a real relationship.  
“Hilltop are due to call, wanna cut a deal. But their CEO Gregory is a fucking coward that prefers to do this shit over the phone instead of face to face. God knows how long that shit is gonna last,” Negan explained.  
I headed over to him, sitting on the edge of the desk. Negan glanced down as the skirt of my dress rode up a little revealing more of my bare legs.  
“Anything I can do to help you prepare?” I asked, smiling softly. 

“No, I got it. Just wanted to make sure I saw you today.”  
He kissed me softly before taking in my outfit. I sat up a little, sticking my chest out and crossing my legs. His smile turned into a grin.  
“You brought this yourself baby girl?” He asked.  
“I thought you’d like it.”  
“Oh, I do. Its sweet when you make yourself look all pretty and dress up for daddy.”  
Well I knew where this was heading now. Even though I had prepared myself for that the second I had entered his office. Negan’s thumb traced my lips, pulling away when I tried to take it in my mouth. He glanced at this thumb for any traces of lipstick, thanks to all this money I could get a long lasting one, this shit was not moving. 

“You wear lipstick like that and I’ll think you have something in mind,” he smirked.  
“Maybe I do. I can’t go back to work looking like a fucked-out mess.”  
“No, you can’t.”  
He kissed me again, harder this time and forced my legs open so he could stand between them. Negans lips worked their way down to my neck, a jolt of heat going straight to my core. I grabbed him through his suit trousers, earning a soft groan from him. He was already semi hard.  
“I wanna see these pretty red lips wrapped around my cock baby girl,” he spoke.  
I smiled knowingly, that’s why I’d warn this lipstick in the first place. I gave him a soft push back so that would sit down in his chair. 

Before getting myself caught up in a lusty haze I needed to think. If we were going to do this we had to take every precaution nessacary. I climbed off the desk only to position myself on my knees under it. The desk would allow me the nessacary cover in case someone walked in. I placed my palms flat on his clothed thighs, slowly working my way up to his belt. I unbuckled it and loosened his trousers. I pulled his cock free from the confinements of his boxers and pressed a soft kiss to the tip. Negan moved his chair closer to the desk and watched as I took his cock in my mouth. He groaned softly, tangling his fingers in her my and making me take more.  
“That’s a good girl,” Negan praised. 

His hips bucked a little, forcing his cock to the back of my throat. I gagged, tears pricking at my eyes but I kept it together, regaining control over my breathing. I began a slow, teasing pace wanting to drag this out as much as I could, wanting to be the one to tease him for a change. Negans grip on my hair tightened and he pulled me off his cock.  
“You gonna act like a brat baby girl, then you’ll get treated like one and I’ll fuck you throat raw,” he threatened, his voice a low growl.  
I bit my lip, part of me wanting to keep teasing to see if he would actually do it. Negan assessed my reaction and a wolfish grin slowly spread across his face.  
“Oh. You do want me to use your throat like a good for nothing whore?” 

Negan forced my mouth open before guiding me back down on to his cock, making me take as much as I could. He thrust into my mouth quickly, barely giving me time to regulate my breathing whilst using my hair to pull me back and forth on to his cock. The pace was rough and my scalp stung but I liked it. I liked him using me for his own pleasure, my one purpose being to make him cum.  
“Your mouth was made for this baby girl,” he groaned.  
My heart swelled at the praise once more, I think it was safe to say I had a praise kink. Negan continued to groan and give me filthy words of encouragement until the phone rang. 

He stopped what he was doing, allowing me to breathe properly. I was unsure what to do, stay under his desk or go. It could be an important call and the last thing I wanted to do was distract him. Negan answered the phone, holding it to his ear. I noticed his face drop.  
“Gregory, I didn’t expect you to call until after lunch,” he almost growled, clearly annoyed.  
Oh, this was a naughty idea that could get me in lots of trouble but it was worth it. I teasingly licked over his head once more, pulling away as his hips bucked for more. I heard him sharply inhale and he reached down with his free hand to swat at me. I shrank back, covering my mouth so that I didn’t giggle too loud. 

I took the head in my mouth again before quickly taking the rest of him in my mouth. Negan slammed his fist on the desk as he did his best to hold back a groan.  
“Everything’s fine Gregory,” Negan reassured him.  
I resumed my pace, using my hand at the base of his shaft. Negan let out a soft growl, masking it with a cough. I smiled to myself, I was going to be punished like hell after this but this was too much fun. He continued to talk about boring business stuff, his voice wavering at times as he struggled to hold back moans or the pleasure became too much in that moment. His free hand came back under the desk, grabbing a fistful of my hair and pushing me further down onto his cock. 

He must be getting close, thinking that once he came it would be over and done with. Thankfully the phone call was coming to an end too, meaning he’d actually be able to enjoy this more. Finally, Negan put the phone down and began fucking my throat once more.  
“You wait till I’m fucking done with you baby girl,” he growled.  
A few more thrusts and he came down my throat, letting out a few curse words through gritted teeth. I swallowed his load before licking him clean. Negan tucked himself away and made himself look presentable once more. I climbed out from under the desk, nervously awaiting my punishment. Negan got to his feet and took my wrists in his hand. He restrained them behind my back and spun me round, forcing me down and pinning me to the desk. 

I made a small sound of surprise, arousal running through me again at his roughness. He bound my wrists together with his tie, this situation being all too familier. Negan pulled the skirt of my dress up and over my rear before pulling my panties down to my ankles.  
“I think twenty spanks is enough, don’t you?” The question was rhetorical, I didn’t get a choice in this after what I’d done.  
“Yes daddy,” I replied.  
“And you’re going to fucking thank me after every single one.”  
I closed my eyes, waiting for the first one. I could take the first few easily, when it started to get to double digits however that’s when the pain really started to set in. 

Finally, he brought his hand down, a light sting spreading across the skin.  
“Thank you, daddy,” I remembered.  
Satisfied Negan brought the same hand down on the other cheek to spread the pain. I moaned softly, enjoying the slight sting for now. I continued to thank him, my voice beginning to waver around the ninth spank. My nails were starting to dig in to my palm and I was biting down on my bottom lip hard. Negan delivered the next three spanks in quick succession. I made a small sound of pain, flinching away from his touch.  
“Ah ah, come on baby girl. You’ve been doing so well and you don’t want to start over again, do you?” He asked.  
“No daddy.”  
“Then back to it.”

His hand rubbed over the marked flesh in a soothing manner. I relaxed into his touch, hoping that if I made it through this that I would get some sort of reward. I pressed my body further into the desk, feeling my legs starting to shake as I struggled to hold myself up. Finally, we reached the last spank, my ass probably bright red with his hand print spread across my ass like a tattoo. Negan untied my wrists and turned me round to face him gently.  
“You ok, baby girl?” He asked.  
I nodded, forcing a smile. He cupped my cheek and kissed me softly, stroking my hair with his other hand. 

“Let’s get you all cleaned up, its gonna hurt to sit down for a while baby girl but that’s what happens when you misbehave,” Negan explained.  
Wait, that was it? No more. He wasn’t going to touch me at all? I felt my heart sink in disappointment. He tilted my chin so that I met his gaze.  
“When you misbehave you take your punishment like a good girl, when I’m feeling like you’ve learnt your lesson then and only then will daddy touch you,” he continued.  
I let out a soft whine, this wasn’t fair.  
“You can act like a little brat baby girl but it won’t help. Now back to work.”  
He kissed me once more before helping me look presentable once more. 

Negan watched me leave his office, making sure I did actually leave and not hang around to try and convince him. I headed to the bathrooms to make sure my makeup was still ok and my hair didn’t look to messy before actually going back to my desk. I sat back down carefully, trying to find a position that was comfortable. I unlocked my screen and saw a new message from Negan.  
_No touching yourself either. Good girls wait patiently._  
I made a small frustrated sound, doing my best to not think of the raging heat between my legs and the discomforting heat on my ass.


	12. Chapter 12

Chapter 12

Negan’s P.O.V

Roxy was round again this weekend. She hadn’t been allowed to cum Monday after the stunt she pulled so I could tell she was more than eager to go to the bedroom. However, with what I had planned I’m sure that would change. She dumped her overnight bag on the floor, her side of the bed. I kissed her, my fingers in her hair to hold her in place as I claimed her lips. We hadn't seen each other much this week, I'd been too busy.   
“Have you been a good girl?” I asked.  
“Yes daddy.”

“I hope so because good girls get rewards and I’m sure after Monday you’re just aching for daddy to make you cum.”  
She nodded, biting her lip. I kissed my way down her neck, before pulling her shirt over her head. I continued undressing her until she was completely bare.  
“Lie down for me baby girl,” I ordered softly.  
She eagerly claimed on to the bed, making herself comfortable. I headed to my wardrobe and opened my toy drawer. I produced a pair of handcuffs, a spreader bar and a body wand which I had made sure to fully charge the night before.

I cuffed both her wrists to the bed before attaching the spreader bar to her ankles. This would stop her closing her legs when I got too much. I leaned down and kissed her once more. I turned the body wand on and pressed it her clit. She moaned and bucked into the toy, her eyes closing in bliss already. I’m sure it wouldn’t take her long to cum the first time.   
“That feel good baby girl?” I asked.  
“Y-yes daddy,” she moaned.  
“Good. You earned this baby girl.”  
A soft smile spread across her face before her lips parted again as she moaned. 

“Maybe I should have you do a bunch of errands for me in the office with this on and held in place by your panties. See how many times you soak them through,” I suggested.  
Roxy could only moan in response, her fists balled and her nails digging into her palms. Roxy’s knees tried to pull together but the spreader bar kept them apart. She cursed and threw her head back, her back arching as she continued to be brought closer to her much needed orgasm. 

Finally, her first orgasm crested, forcing a shrill cry from her lips as it completely washed over her body. I watched her hole clench where it was desperate to be filled. I’d fuck her later once she’d recovered. I didn’t take the viberator away to give her a break. Roxy jerked harshly as it began to get too much on her clit. She let out a whine, her eyes shutting tight as she became overstimulated but I wasn’t going to stop. This is what she gets for being so needy. Maybe she’d think twice now when she begged me to make her cum. I know this was the opposite of her recent punishment but she was enjoying herself. 

Roxy bit her lip, the pain would give way to pleasure. I pulled the bod wand away a little so that it was ghosting across her clit. Soon enough the pleasure came back and she was moaning and panting again. I smiled and pressed the toy back against her clit. Roxy moaned my name, her hips bucking against the object as another orgasm quickly began to build. I only had it on the second setting, the first wouldn’t be enough and the third would be too much. Roxy threw her head back, cursing loud as she reached her second orgasm. As quick as it came, it quickly faded and overstimulation hit her again.

Roxy arched away from the toy, whining from the feeling.   
“D-daddy, please. I – fuck…I cant-“ She managed, her voice strained.   
“You were so desperate to cum baby girl. I thought I’d give you one for every day that you didn’t touch yourself this week.”  
She whined again. I smirked and leaned down to kiss along her collar. Her chest was heaving by now, her breathing laboured as she did her best to hold it together. Roxy was staring to shake, tears pricking the corner of her eyes. She knew the safe word, until she used it I wasn’t going to stop. I altered between watching her face twist between pleasure and discomfort and watching her hole clench around nothing as she came. By now I was as hard as a rock, but this wasn’t about me. I would get what I needed later. 

Roxy reached her third climax with a pathetic whimper, her hips jerking violently. She was completely soaked by now, she could take a shower once she regained some energy. I forced a final orgasm from her before finally turning the toy off. Roxy lay there, breathing heavily with her eyes shut. I kissed her forehead, giving her the praise she needed. I carefully removed the cuffs and spreader bar before laying down next to her. I pulled her into my arms, which she eagerly excepted. I stroked her hair, kissing her cheeks.   
“You did such a good job baby girl, daddies so proud of you,” I spoke softly.   
A soft smile spread across her face as she continued to relax into me. Maybe I’d run her a bath. Pamper my little baby girl because of how well she did. I’m sure she’d like that. 

\------------------------------------------------------------------------------------------------------------------------------------

After an hour’s nap Roxy slowly woke up, untangling herself from me. I headed to the bathroom to run her that bath, adding a bunch of salts and bubbles to the water. Roxy eventually padded into the bathroom, still naked and a little sleepy.   
“Come get in the bath baby girl, let daddy take care of you,” I smiled.  
She returned the smile and I helped her into the bath. I removed my own clothes and got in behind her, pulling her close again. I liked the feeling of having her in my arms. As much as I enjoyed the sex I was starting to enjoy these little moments with her, the tender moments. Perhaps I was getting too attached already. 

I shook the thoughts free and grabbed some shampoo, squeezing some into my hand and rubbing it in to her scalp. She rested her back against my chest, letting out a relaxed sigh as I massaged her scalp.   
“Heaven and hell night is next week, right?” She asked.  
“It is. You still up for it.”  
“If you are.”  
“I’ll have our costumes sorted again.”  
“I look forward to it. Although I’m also dreading what Simon might be wearing this time.”  
“He does like to be pretty out there with his costumes. You’ll get used to it.”  
I carefully washed the shampoo out of her hair, before going through the same process with conditioner. 

Roxy glanced at the bottle of shampoo and frowned, “how expensive is that stuff, I feel like I just went to a salon.”  
“Only the best for my baby girl.”  
She smiled and I kissed her cheek. We waited till the water started to cool before getting out and drying ourselves off. Roxy dried her hair and changed into clean clothes. I put on some lounge wear and we headed to the kitchen for lunch.   
“I want you to do something for me baby girl when you get a chance,” I started.  
“Ok?” She raised an eyebrow.  
“Make a Wishlist for me on Amazon, anything you want. I’ll get it for you, that way I can still spoil you and you’ll get surprise gifts.”  
“I can do that. But don’t expect anything too exciting on there.”  
“I’m sure you can find something exciting for me.”  
“Is that a challenge?”  
“Perhaps.”


	13. Chapter 13

**Summary for the Chapter:**

> I apologize for my absence, I havent had much muse in writing Negan what with the shit show season 8 was. Im trying my best.

Chapter 13

Roxy’s P.O.V

Saturday night arrived and Negan and I were wearing out costumes. Negan was dressed in a red, tight fitting suit, black leather gloves and had attached small horns to his forehead using some liquid latex and makeup. He’d gone all out and added red contacts too. Whilst his costume covered him pretty much head to toe. Mine didn’t. I expected this but still rolled my eyes when he’d shown me. The ‘costume’ consisted of matching white lacy underwear, complete with stockings and heels. The only part that made me an angel were the white feathery wings and white halo for my head. Negan produced a collar, putting it round my neck. The chain would be attached later. An angel that had been captured and corrupted by a devil. Seemed fitting. 

Negan and I arrived at the club around 8pm, the club already half filled with other people dressed like angels and demons. There were a few fallen angels around. Simon was not hard to spot at all. He was only wearing white boxer shorts and angel wings. Of course, I should have expected that. It was safe to say he took good care of his body though. Negan caught me staring and cleared his throat.   
“I thought you said you weren’t into sharing,” he spoke.  
“I’m not. I’m just admiring.”  
“Would you be against him joining us in some way?”  
“Depends on how he would be joining us.”  
“Simons very much into voyeurism.”

This took me off guard, he didn’t seem the type to simply get off from just watching. I figured he’d want more involvement than that.   
“Maybe a few more months down the line. I’m still getting used to doing this whole thing,” I explained.  
“No rush baby girl. Besides he’d have to be up for it himself.”  
Simon spotted us and waved before giving thumbs up at the costumes. Negan attached my collar and kissed my cheek.   
“So, what would you like to do first baby girl?” He asked.  
I glanced around the room, taking in the various stations and the crowds around each one. I bit my lip, trying to decide and work up the courage to try one. 

“How about a drink first?” I suggested.  
“Sure.”  
Negan led me over to the bar and ordered us two drinks. I downed my drink, needing the liquid courage.   
“So maybe we could try the flogging stuff,” I shrugged, trying to play it off as if it were the most casual thing in the world.   
“If that’s what you want baby girl.”  
Negan led me over to the flogging station, finding a free spanking bench to help me on to. I was on all fours, my back to the other participants. The only thing to look at was the wall in front of me.   
“You want me to start off with my hand or go straight for the riding crop?” Negan asked.  
“Maybe you could start with your hand.”

I had barely any time to finish my sentence before Negans hand came down on my rear. I gasped at the feeling, although it wasn’t too bad with my panties still on. Negan brought his hand down again, harder this time. I bit my lip, holding back a soft moan. After a few more he pulled down my panties so they were around my thighs, all of me now exposed to anybody now watching. Thank god, they couldn’t see how hard I was blushing.   
“Looking good baby girl, keep this up and daddy will give you a reward,” he praised.   
I smiled to myself, feeling a bit more confident. I had wanted this. And now it was finally happening, on display for everyone to desire and have dirty thoughts over. Yet they couldn’t touch me or have me because I belonged to Negan. His hand came back down on my rear one more time before giving me a short break to grab a riding crop. 

I gasped at the sudden feel of cool leather running down my rear and cooling the areas he’d spanked over.   
“Seems we’ve gathered a little crowd baby girl. They seem to like your ass almost as much as I do,” Negan continued.   
I looked over my shoulder to find a small handful of people, men and women watching. I bit my lip, feeling my cheeks burn again. They couldn’t take their eyes off me. I was the centre of attention, the object of their desire. I turned back to the wall before Negan tapped my rear with the crop lightly. Probably to get me used to the feeling. He brought it down again, a little harder but still not enough to leave that stinging sensation.   
“You think you can take ten baby girl?” He asked.  
“Yes, daddy.”  
“Good girl.”

I took a deep breath and relaxed to prepare myself from the next set of blows. The riding crop came down with a slapping sound, a small sting spreading across the area. It wasn’t as bad as his hand; his hand was bigger meaning he could inflict more pain. But the riding crop was smaller and demanded more control for precision. My ass was still going to be sore after this, but probably not as sore if he continued to use his hand. By now Negan was up to five, the pain still bearable even as he continued to spread it. I bit my lip, making a small sound as he brought the crop down across my thigh. My head fell forward, repositioning my hands to brace myself better. I took a deep breath to work through the hot line of pain across my thigh, the sensation turning to a dull throb. Negan brought the crop down on the back of my other thigh, earning another sound from me. 

Before I had time to adjust to the pain he brought the crop down again, forcing a whimper from me. Thankfully he reached ten, giving me, one finally blow from the crop. I relaxed, my breathing noticeably heavier. Negan put the crop back and ran his hands across the marks he’d left on me. The cool feeling of his leather gloves helped to soothe the pain.   
“How about that reward baby girl?” He asked.  
“Yes, please daddy,” I spoke, my voice pathetically desperate.   
Negan chuckled and helped me on to my back so that I was in a more comfy and relaxing position. Like this I could see the people watching us, waiting just as eagerly as me for Negans reward. Negan kneeled in front of me, taking my legs and positioning them over his shoulders. I bit my lip, anticipation and lust building as I waited for his tongue. 

Negan kissed my inner thighs, teasing me further. I whined, my hips bucking. Negan chuckled at my desperation before sucking a purple mark into my thigh. Finally, he gave me what I wanted, his tongue lapping at my clit. I moaned, my back arching at the blissful feeling. If I could have this man between my legs 24/7, I would. I tangled my fingers in Negans hair, tugging a little. He growled against me, sending more delicious sensations through my clit. I shuddered as he slipped a leather clad finger into my wetness. I glanced back at the slowly growing crowd, noticing a dark-skinned woman with dreadlocks, dressed like an angel, the white looking beautiful against her dark skin. Her eyes locked with mine, seemingly ignoring what I guessed was her submissive. The submissive was a blonde who looked to be in her 30’s and was dressed as a devil. The blonde was trying her best to get her dom’s attention but the dom was much more focused on me. 

Negan brought my attention back to him as he slipped a second finger into my heat. I moaned, pleasure continuing to build. He traced various patterns on my clit with his tongue, some shapes I could make out if I focused hard enough. Negan crooked his fingers against my sweet spot, the feeling of the leather adding to the sensation. I moaned his name, my fingers tangling in his hair. He started to trace out the letters of his name on to my clit as if marking it as his property. My moans got louder, my eyes shutting tight as my orgasm continued to build. A few more flicks of his tongue and I reached my climax, waves of pleasure running through me as I cried out his name. It’s like in that moment I had forgotten about our audience. 

Negan licked me clean, stopping when I jerked away due to stimulation. He sucked his gloved fingers clean before helping my sit up. The onlookers had dispersed, a few remaining. Two being the dark skinned dom and her submissive. She was still eyeing me up as if she wanted me for her own. Maybe if I hadn’t already been claimed I’d say yes. She was beautiful. Negan pulled my panties back into place and kissed me, his fingers in my hair.   
“You alright baby girl?” He asked.  
I could only nod in response, still coming down from my high and breathing heavily. The dom approached us, tugging her sub along. She smiled, showing a row of perfect white teeth. That smile was stunning, I felt my heart swell at it. 

“That was a nice little show you put on,” She spoke.   
“Thank you, we’re glad you enjoyed it so much,” Negan replied politely.   
“I’m Michonne, this is Andrea. We were hoping to offer you a proposal.”  
My interest perked up at the word ‘proposal’. What could she have in mind?   
“I’d like to play with your submissive. If you would allow that and if she would be comfortable with that.”  
Negan rubbed his stubble, as if thinking it over. We knew sharing was a no. We would remain exclusively each other’s for however long this continued. Even if the thought of her playing with me was an appealing one. Maybe later, when Negan and I were more comfortable with the idea.   
“I’m afraid we’re not quite at the sharing stage just yet. Roxy’s still fairly new to all this, I’m trying to ease her in gently,” Negan explained.  
“Of course, because what you just did was gentle,” Michonne smirked. 

Negan shrugged, chuckling. Michonne and Andrea left us too it, heading off to another station. Hopefully we’d see her again. Negan led me over to the bar and got me some water, before kissing my forehead.  
“I’m so fucking proud of you baby girl. You did such a good job tonight,” he praised again.   
Simon was at the bar as well, shaking his head at the both of us with a smirk on his face.   
“You just had to be the centre of attention, didn’t you?” He asked Negan.  
“Don’t act jealous Simon,” Negan replied, “you didn’t have to watch.”  
“Oh please, as hot as that was, I’m sure both of you could do much better.”  
“Well maybe one day there will be an open invite for more. If Roxy would like that.”  
I bit my lip, it was obvious Simon was into voyeurism. I had just let a whole bunch of strangers watch as Negan ate me out, would there be much harm in Simon watch as Negan fucked me? 

Probably not.   
“I’m ok with it,” I smiled.  
Negan returned my smile before turning back to Simon, “just watching though. Sharing is off the table.”  
“I hear ya, loud and clear. But hey when sharing is on the table I’d like to think you’d call me first.”  
“Michonne’s already called first dibs, seems like you might have to get in line.”  
Simon tutted. Negan kissed my cheek, his hand on the small of my back. I stepped closer to him so that I could rest against his chest. Negan kissed his way up my neck to my ear.   
He whispered, “don’t get tired baby girl, I’m not done with you yet.”


	14. Chapter 14

Chapter 14

Negan’s P.O.V

I glanced at the wall clock and sighed. Roxy was half an hour late for work. I guess everything I’d had planned for today needed to be changed. She’d have to be punished instead. I picked up my phone and found her number in my contacts. I pressed the dial button and held the phone to my ear. She answered on the fifth ring.   
“Hello?” She spoke, her voice sounding weak and hoarse.   
I frowned, “you ok baby girl?”  
“Did they not tell you that I called in sick?”  
Communication in this place really needed to be worked on, “no they didn’t. What’s wrong?”  
“I think it’s just a stomach bug or something.”

I glanced at the clock again, “you want me to come over after work?”   
“No. No. I don’t want you to get it if it’s contagious.”  
“Alright, but you call me if you need anything ok baby girl.”  
“Ok daddy.”  
We said our goodbyes and I hung up. I would have preferred her to text me as well as call in sick. It would have been nice to know. Oh well. I stop by when I finished my shift to make sure she was ok. Even if she didn’t want me round, I had to make sure she was ok. Not many sugar daddies looked after their sugar babies in this way. I’d get her some soup, plenty of water and maybe a movie we could watch together. Anything to make her feel better. 

\------------------------------------------------------------------------------------------------------------------------------------

Finally, my shift came to an end and I power walked down to the carpark. The sooner I got out of here the better. I’d placed an order for soup takeout, with some noodles as well. Just in case the soup wasn’t quite enough for her. I swung by the rental place first, grabbing a DVD off the shelf at random. It was new and I hadn’t seen it. I’m pretty sure we could entertain ourselves if it was shitty. I then picked up dinner and drove to Roxy’s apartment complex. I grabbed the things and headed up to her floor. I rang the doorbell and waited. I heard movement from inside. 

Roxy opened the door, wearing pj’s and a big fluffy dressing gown. Her eyes, nose and cheeks were red and she looked exhausted, her hair a unbrushed mess. She frowned at me.   
“I told you not to come round,” She spoke, her voice still small and weak.   
“I know you did, but I wanted to make sure you were ok. I brought dinner.”  
Roxy inhaled the scent of the meal and smiled, “whatever it is, it’s making me hungry. I just hope I’ll be able to keep it down long enough to enjoy it.”  
She stepped aside and let me inside, closing the door behind me. I put the takeout bag down on the kitchen counter and looked around her apartment. 

Roxy started tidying up various things, as if to make it look a little better. This place was…a dump. It was tiny, with barely any room for two people let alone one. I needed to get her a new apartment. Although I’m pretty sure with the money I was giving here she would be able to afford a new place soon enough. Roxy looked embarrassed that I was here, seeing her living space.  
“I know, its shitty. But it’s all I could afford,” she shrugged.  
“It’s cosy,” I said, trying to sound positive.  
“It’s suffocating. Why do you think I like your place so much?”  
I smiled and kissed her forehead. This seemed to put her at ease. She picked up the DVD, flipping over the case to read the back of it. 

“I didn’t think you were in to chic flicks?” She smirked.  
“I picked up the first one I saw. Honestly.”  
“I can tell. You have good movie taste normally. This…not so good.”  
I shrugged, getting out dinner for both of us. Roxy looked over my shoulder and smiled to herself.   
“You got me soup?” She asked.  
“And noodles.”  
“Thank you, daddy. I didn’t think you could be so sweet.”  
I wanted to ask her what she meant by that but didn’t have much of a chance as Roxy grabbed her food containers and made her way to the couch. 

I put the DVD in and sat down next to her with my own food. Roxy was already tucking into her food, it was clear she was hungry. We started the movie, managing to pay attention for the first half an hour. I see what she meant though, this was bad. Roxy and I finished our food and already she seemed a lot better in herself. I put my arm around her and pulled her close.   
“What did you mean earlier?” I asked.  
“Hm?”  
“You said you didn’t think I could be so sweet.”  
“Oh. Uhm. Well, it’s just I’ve never seen this side of you before. Not that I’m complaining. I’m just so used to how dominating and sexual you are. I didn’t think taking care of me like this was part of our arrangement,” she explained.  
“It is. It’s not just sex all the time, I enjoy your company.”

Roxy smiled wider, “I enjoy yours. I really do look forward to the weekends with you.”  
“I’m glad to hear it.”  
“I’m sorry I look like a mess-“ she began.  
“You don’t need to apologize for being sick.”  
“I just feel like I need to impress you all the time. We both live such different lifestyles. I guess I’m just worried you’ll get bored of me or something like the state of my apartment or myself will change the way you see me.”  
I took her hands in mine, forcing her to look at me.   
“Baby girl. You don’t need to impress me. You did that the moment you walked into my office for that interview. Your beautiful no matter what you wear or how you look,” I reassured her.   
“I’m sorry to bring all this up, I guess being sick makes me anxious as well.”

“You feel like your gonna throw up? Or has the soup helped?” I asked.  
“Well its staying down for more than five minutes, I think that’s a good sign.”  
I kissed the top of her head again, before she rested her head on my shoulder. There was an event coming up next week. A friend from college was getting married and on the invite, it specified a ‘plus one’. I didn’t really have a plus one. Roxy was an option but people would probably think we were a couple. And she might get the wrong idea and think it was a date and that I was starting to develop feelings for her…was I developing feelings for her? Would I have visited any past sugar babies if they were sick? No, so why was Roxy so special? 

Maybe we were spending too much time together and I was getting to attached. She was only in this for the cash, she didn’t care about me. Maybe I should talk this over with Simon, see if he could offer any better advice. I sighed, giving into my feelings. I had to take someone to this wedding.   
“Baby girl, I’ve got a wedding coming up next week and I need a plus one, would you mind coming with me?” I asked.  
Her face lit up at the question, “of course not. I’ll need to find something to wear but I’d love to go.”  
“I can take you dress shopping tomorrow during lunch, find you something nice.”  
Roxy beamed and kissed me on the cheek, squeezing me tight, “thank you.”

\-----------------------------------------------------------------------------------------------------------------------------------------

The next day Roxy was a lot better. Not one hundred percent but there was a clear improvement. She’d made it into work, doing her best to catch up on everything she’d missed. Lunch soon came and we left the building. I drove us down to a quiet shopping complex. I led Roxy inside one of the dress shops and let her pick out some that she liked. I spotted her looking at price tags again and deciding against dress all because of the price. I sighed, when was she going to learn that I wanted to spoil her? I headed over to her and looked at the dress. It was a red silk pencil dress that stopped above the knee. The long red sleeves were made from lace. I could see why she liked it. I found her size and handed it to her.  
“Try it on,” I spoke.  
“Daddy, it’s too much money.”

“Nothing’s too much money for you. Go and try it on.”  
She sighed but didn’t continue to argue. She headed off to the dressing room after finding a few other dresses to try one, likely more cheaper than the red one. Roxy showed me each dress. They were nice and cute but I still wanted to get her that red one. Finally, she pulled back the curtain, wearing that dress. Shit. Wow. Roxy noticed my expression and sighed.  
“You don’t like it?” She asked.  
“Fuck no. Right now, I’m trying to recover from how beautiful you look. God knows how I’m gonna keep my hands to myself on the actual day.”  
She smiled, a slight blush spreading across her cheeks. She did a small twirl in it before looking at herself in the mirror. 

If she looked this good now, I really was going to struggle at the wedding. The dress hugged her figure in all the right places.   
“I think we have a winner, don’t you?” I spoke.  
“I think we do.”  
Roxy changed back into her work clothes and handed me the dress, which I paid for before she could change her mind. Hopefully we’d have enough time before the wedding to have some fun.


	15. Chapter 15

**Summary for the Chapter:**

> I apologize for my absence, writers block hit me hard.

Chapter 15

Roxy’s P.O.V

Negan led me into the dining hall, looking for our name place cards on the many tables. The ceremony had been lovely and of course the bride had been breath taking. Negan found our designated seats and pulled out my chair for me. I smiled and sat down, such a gentleman. He sat down next to me as the rest of the room filled with guests. We were on a table with two other couples, what I’m guessing was people Negan and the groom knew from college. Once everyone was seated and began to mingle with each other the starter came around which was a typical wedding soup.   
“So how did you and Roxy meet?” The red head asked that was sat opposite me.  
I almost choked on my wine, trying to think of a good answer. They thought we were a couple, they thought we would have met under normal circumstances. Well I guess we did until he’d approached me for sex. 

Negan sensed my uneasiness and placed his hand on my knee to calm me, he smiled softly and I relaxed a little.   
“We met at work. Roxy needed to do a health and safety inspection. Make sure everything was in order and well I just couldn’t resist. Figured it’d be better to ask for her number instead of letting her go,” Negan explained.  
The other couples seemed to buy it. Thank god. I also liked the fact he’d twisted my actual job role a little so that I didn’t sound beneath him. Negans hand was slowly sliding higher up my leg and under the skirt of my dress. He stopped at my thigh and I breathed a sigh of relief. I knew our relationship was kinky and all but I didn’t want us to risk getting caught in a situation like this. 

The red head began to tell the story of how she’d met her other half. I did my best to listen even with Negans hand slowly creeping further up my thigh. I pressed my legs together in the hopes of stopping him. Negan forced his hand between my legs, rubbing me through my panties. I clenched my fists, my grip tightening on my napkin. He pushed my panties aside and started circling my clit. I bit my lip, doing my best to focus back on the story being told. Negan’s fingers eventually slipped lower, teasing my entrance. I let a heavy breath, trying to mask it as a sigh. Do not fucking moan. Our second course was brought to us and I relaxed a little. Negan would need both hands to eat. Oh, how wrong I was. 

His hand remained between my leg alternating between rubbing my clit and teasing my hole. God, I wanted so much more but I needed him to stop. I couldn’t hold back the soft groan, doing my best to mask it with a cough. This still gathered the attention of the table, concerned looks being thrown my way.   
“Are you alright baby girl?” Negan asked.  
I nodded, taking a sip of wine. He still didn’t let up however, instead he increased his pace. I gripped the edge of the table, feeling the need to buck into his touch. I tensed up so that I would stay still. I just needed to get out of here, five minutes to escape him and calm myself down. 

Negan stopped touching me for a few seconds to dig his fingers into my thigh, hard enough to bruise and keep me in my seat. I guess no escape for me. He was going to make me cum in front of all these people. I bit my lip, focusing on keeping my breathing even. Just don’t draw anymore attention to yourself. His fingers moved back up to my clit, resuming rubbing it in a circular motion. One hand gripped the edge of the tablecloth, my knuckles starting to turn white. I was torn between wanting to cum and wanting him to stop but if I made him stop he might punish me later.

Negan applied more pressure to my clit, almost forcing another moan from me. I grabbed my napkin and pretended to clean my lips with it as I let out a soft whine. A thought crossed my mind, a way of revenge. I could drop my fork and dive under the table cloth to retrieve it, maybe take Negans cock in my mouth whilst I was under there. See how he'd like it. I felt my fingers loosen around my fork in temptation. This was just like when we'd gone out for dinner and he'd used the vibrating panties on me. I couldn’t decide which was worse. I glanced over at him, he was casual, finishing his main course and listening intently to the story being told by the red head.

Fucking Oscar winner there. I stifled another moan as I could feel my orgasm being to build. How the fuck was I expected to cum quietly? I gripped Negans forearm, meeting his gaze and shooting him a look that begged him to stop. He smirked, his pace speeding up. Fuck.   
“You alright baby girl?” He asked soft enough so that only we could hear in a slightly mocking tone.  
I wanted to say something but I knew it would just come out as a moan and he knew too as his smirk grew. He leaned over, placing a kiss on my cheek. His lips moved up to my ear.  
“Cum for me baby girl, cum for daddy in front of all these people,” he whispered encouragingly.

As if on demanded my orgasm peaked, washing over me and making my hips buck into his touch. I bit my lip, holding back the cry that wanted to escape. I averted my gaze to my plate, hoping nobody had noticed. If they had I think I would die of embarrassment even if I would likely never see these people again. Negan stopped, using his napkins to clean his fingers. I made sure to breath slowly instead of panting and making it obvious. Thankfully when I returned my attention to the table nobody was looking at us, they were all looking at the red head who was still blabbering on. 

I relaxed a little in my chair, smiling to myself. Negan smiled and kissed my cheek again.   
“You did such a good job baby girl, daddies definitely gonna fucking reward you later,” he promised.   
Oh, I had no doubts about that.


	16. Chapter 16

Chapter 16

Negan’s P.O.V

Roxy was due round again this weekend. I was a mixture of excited and nervous. I felt we were going too far, I was getting into deep. I couldn’t allow myself to fall in love again, she’d just break my heart like the last one. The only one. It had been five fucking years and it still hurt to think about her. I wouldn’t be good enough for Roxy, not a good enough boyfriend. I was only good in the bedroom, I was good at fucking not loving. Part of me felt like calling her and making up some bullshit excuse for her not to come round. We’d spent every weekend for the past three months together. She slept round each weekend, it was starting to feel…normal. I needed to clear my head, needed someone to rant and vent too. 

Just one weekend away from her couldn’t hurt. I saw her five days a damn week at work. I grabbed my phone and checked the time and for any messages or calls. Nothing. First, I’d text her. It would be better than hearing the disappointment in her voice.   
_Hey baby girl. Hope you’re ok. I’m sorry to be an ass but I’m gonna have to cancel our plans for the weekend. I got a business trip to go on which I unfortunately can’t skip. I promise to make it up to you next time._  
I read it over a few times before sending it. I felt awful standing her up like this. Hopefully Simon was free. I opened up the messages between him and I.   
_Hey, you free today?_

I put my phone in my pocket, walking away from the kitchen counter unsure what to do with myself. My phone buzzed as I reached the lounge. I pulled it out finding a message from Roxy. I felt my stomach drop once again. Why the fuck was this so nerve wracking? I knew how to talk to women, I knew how to deal with women. I shouldn’t be scared of what she had to say. If she didn’t like my ways then she could go elsewhere and I could find someone else easily. Even if it wouldn’t be the same. I opened the message.   
_That’s ok, it can’t be helped. I’ll miss you daddy. Don’t work too hard. Xxx_  
I smiled softly at her words, she’d taken that better than I’d thought. God, she was fucking sweet and understanding. 

My phone buzzed signalling another text message. Simon.   
_Yeah, what’s up?_  
 _I’ll explain when I get to the club._ I replied.  
With that I grabbed my car keys and locked up the house. I reached the club in less than twenty minutes and headed round the back, knowing that would be the only entrance that would unlocked at this time of day. I remembered the door code and headed inside. I found Simon at the bar, preparing various spirits and bottles for next week. I sat down at the bar opposite him and he produced two empty glasses.   
“The usual?” He asked.  
I nodded and he pulled down a bottle of Scotch, pouring a decent amount in my glass. 

“So, what’s the problem? Girl trouble?” Simon asked, “isn’t it always girl trouble?”  
I shot him a look as I took a mouthful of the alcohol.  
“I feel like I’m getting in to deep,” I spoke.   
“And why is that such a bad thing?”  
“You know why it is.”  
Simon sighed and refilled my glass, “you really think Roxy’s gonna do what that bitch did?”  
“You were the one who told me most women are the same.”  
“To make you feel fucking better. And you missed the key word there. Most women. Not all women.”  
“What does it fucking matter? Roxy’s probably sleeping with me because I give her a shit tonne of money for it.”

Simon raised an eyebrow, shooting me a look, “that is usually how those arrangements work. But you honestly think she’s that shallow?”  
“I don’t know what to think.”  
“Lucille was five fucking years ago. You think she still thinks about? No, she’s gotten on with her life with that fuck she left you for. Not every woman is gonna screw you over like she did. If your too scared to have a real relationship then you should stop taking on sugar babies. You wanna break things off with Roxy then you do it now before you do any real damage.”  
I paused, putting my glass back down on the bar, “what the fuck does that mean?”

“You need your eyes tested or something old man? Or are you blind? Have you not seen the way she looks at you? How eager she was to please you and try something out just to impress you around here. You could ask her to do anything and she would. There’s something there. I suggest going for it before she thinks you’re the one that’s not interested.”  
Another pause. I hadn’t really thought about it, or I probably hadn’t noticed. Simon downed his drink, letting me think it over.  
“You think she’d really want more?” I asked.  
“How about you fucking ask her? I don’t have a set of crystal balls.”  
“I’ll ask her next weekend.”  
“You need to ask her now. You leave it and you’ll lose your fucking balls.”  
He wasn’t wrong about that. I’m sure if I didn’t ask her today or tomorrow then that doubt and fear would come back worse than ever. But what if she said no? I don’t think I’d be able to handle that.

“I’m not asking her for you. You possess a pair of balls yourself. And make sure you do it face to face. If I’m wrong, which when have I ever been wrong, you break it off and you don’t ever have to see her again,” Simon explained.  
“Your right,” I mumbled.  
Simon smirked and leant forward a little as if he hadn’t heard me, “what was that?”  
“Go fuck yourself.”  
“Might do later. Anything else you need? Or you done drinking my liquor and getting my advice?”  
“Well I’ll take the bottle if you’re not too attached to it,” I smirked.  
“Go home, call her round and tell her.”  
“Yes sir.”  
“Careful, I like that,” he joked.

I got up from the barstool, we said our goodbyes and I left heading back home. I sat down on the couch and stared at my phone. I had to call her and tell her. But she’d know I’d been lying about the business trip and that probably wouldn’t go down well. I couldn’t tell her. Not until I next saw her. but that would be at work and what if someone overheard us? Work was the wrong place to tell her. It really would have to wait till next weekend.


	17. Chapter 17

Chapter 17

Roxy’s P.O.V

I was eager to see Negan this weekend what with him having to cancel last week and then we hadn’t been able spend much time at work. It almost felt like he'd been avoiding me, or maybe I was over thinking the situation. I parked in the drive way, stopping myself from running to the door. I missed just being able to spend time with him and talk to him. Sex was just a bonus today. I rang the doorbell and he answered after a minute, smiling at me. He pulled me into his arms and kissed the top of my head.

“God, I missed you so much baby girl,” he spoke.  
“I missed you too daddy. I've been looking forward to seeing you.”  
Negan led me inside the house, taking my bag from me. He left it in the bedroom, kissing me once more.  
“I think you should start leaving some of your things at mine, save you bringing a bag every time,” he suggested.  
Well that was always a good sign seeing as I wanted this relationship to start moving forward, I just hoped he wanted the same thing. But he was too difficult to read at times. I couldn’t tell if he felt the same or I were just another sugar baby to him.

I was also too afraid of bringing it up. The fear of rejection was the worst. Negan would likely not feel the same way. I mean he was just paying me to fuck me so why would he want anything else. I was disposable at any moment that he got bored. Perhaps I should try harder to keep his interest. I kissed him, tangling my fingers in his hair and nipping at his bottom lip as if to prove my point. He smirked, holding me close as one hand grabbed my rear.   
“You missed daddy that much huh baby girl?” He asked.  
I nodded, playing a little coy. His smirk turned to a grin. He returned the kiss, kneading the flesh of my ass through my jeans. 

“I got something new for us baby girl, something I’m eager to try out with you,” he announced.  
I smiled, clearly interested. Negan took my hand in his and led me out of the bedroom and further into the house. He led me to one of the spare rooms, one that he was debating what to do with. He had plenty of guest’s rooms as it was so he didn’t want to make another one. But he also didn’t want any guests finding a playroom. He opened a door, revealing a playroom in the making. I guess he’d changed his mind after all. Not that I was complaining. The walls were a dark wine red, a four-poster bed in the middle of the room. 

There were various chests of drawers and wardrobes, which I’m sure were filled with all kinds of goodies. From a less, kinky persons point of view it looked like just another bedroom. That was until you spied the Saint Andrews Cross pressed against the left wall. I’d made sure to my research a few weeks back on everything kinky so that he wouldn’t have to explain anything else to me. The Saint Andrews Cross was used for bondage, I remember it had peeked my interest a little when I came across the webpage. The restraints were black leather cuffs, so they would be more comfortable than metal. 

“I know we’ve done bondage before and your probably getting a little bored of it by now-“ He began.  
“You’re never boring. Everything you introduce me to is always exciting,” I reassured.   
It was true. Sex with Negan would never ever get boring. Now that I’d experienced the BDSM lifestyle it amazed me how regular couples didn’t get bored of each other in the bedroom. Negan smiled softly and kissed me on the cheek.   
“You wanna try this out baby girl?” He asked.  
I nodded, biting my lip as my thoughts flooded with so many dirty images. Negan sat down on the edge of the bed.   
“Take those clothes off for me baby girl. Give daddy a show, he’s missed that smoking hot body of yours,” he spoke.

I felt my chest swell with pride and my cheeks burn a little. I thought I’d be used to compliments from him by now but he still had a way with words that made me feel special. I stood in front of him so that he had the perfect view. I slowly pulled up the hem of my shirt, revealing my stomach to him but not high enough to reveal the underwear beneath. I might have gotten some more that I was excited for him to see me in. I pulled my shirt over my head slowly, revealing the 40’s styled bra I’d brought. 

It was black with red ribbon that tied up at the front for decoration. He grinned, looking me over with greedy eyes. Negan knew my underwear collection well enough to know that this was new. My hands moved down my chest, squeezing my breasts teasingly before sliding down to the button on my jeans. I popped the button and slowly pulled down the zipper. My jeans were high waisted as to hide the matching 40’s styled high waist panties underneath. I felt like a pin up girl, it gave me a lot of confidence. 

Unfortunately, there was no sexy way to remove jeans. I pushed them down my hips before grabbing the cuff and pulling them the rest of the way off my legs. I stood before him, letting him take it all in before doing a slow turn, letting him see everything.  
Negan whistled, “well aren’t I the luckiest fucking guy in the world. God damn baby girl.”  
I grinned, turning back to face him, “I’m the lucky one.”  
Maybe subtle hints might work instead. I hope something worked.  
“How’s that baby girl?” He asked.  
I walked over to him before straddling his lap, my hands on his shoulders. 

“Because you’re everything a girl could want. Any girl would be lucky to have you,” I spoke softly.  
“You’ve got me baby girl, no one else.”  
He pressed his forehead against mine before kissing me softly. His hands rested on my hips as the kiss became more heated. Eventually he picked me up, wrapping my legs around his waist and carrying me over to the cross. The wood was a dark chestnut and the cross was more in the shape of an X, so that my arms and legs would be spread apart. There were cuffs for both my ankles and wrists. Negan gently put me on the floor and took hold of one of my wrists, bringing it to the restraint. 

He tightened the strap and worked on the other one. I gave them both a quick test pull as Negan restrained my ankles. I could still stand comfortably like this. Negan stepped back so that he was out of reach, admiring his handy work. He then undressed himself down to his own underwear.   
“I think I might just keep you here like this. It’s quite the view,” he smirked, “although, I do have an idea.”  
Negan opened up one of the drawers and produced a red silk scarf. He put it round my eyes, tying it behind my head. I bit my lip, anticipation building. 

I heard him root around for something else, something clanking against a glass. I frowned, trying to determine what it was. I soon found out as Negan pressed something cold and wet against my neck. I gasped, flinching to get away from the ice. Negan continued to press it to my skin as it melted, water dripping down my chest. He removed the cube from my neck, instead now pressing it to my lips. I opened my mouth a little, water dripping down his fingers. With his free hand he pulled down the cups of my bra, freeing my breasts. 

I bit my lip, knowing exactly where the next ice cube was going. I did my best to prepare myself. Negan surprised me and used his tongue on my nipples first, warming them with his mouth. I moaned, arching into the feeling. He quickly replaced his mouth with another ice cube. I whimpered, biting my lip. It felt odd, but in a good way. My nipples hardened further at the contact. Negan kissed my neck, trailing the ice cube further down and across my belly. By this point I was panting, my body twisting away from the coldness. 

Thankfully Negan ended the torture there. I heard him put the ice cubes back from where he’d gotten them before he was stood in front of me once more. His fingers took the same trail south as the ice cube had, going further and running between my folds. I made a desperate sound, I needed him to touch me. He kissed me softly, the kiss barely there making me want more. I arched my neck to chase him for another kiss but he stepped back out of my reach. He finally touched my clit, rubbing over it softly. If he wanted me to beg, he was going to get it. 

“Please daddy,” I pleaded.  
“Does baby girl need me that bad?”  
“Yes.”  
“I suppose it’s been almost two weeks without daddy filling your perfect little pussy.”  
Negan removed the restraints around my ankles and took hold of my legs, wrapping them around his waist. I felt his hardness against me and stopped myself from bucking against him. I bit my lip and gripped my wrist restraints.   
“Say please again for me baby girl,” Negans lips were near my ear.   
I swallowed hard, making myself focus, “please daddy.”  
“Good girl.”


	18. Chapter 18

**Summary for the Chapter:**

> WARNING: PLEASE READ THIS BEFORE READING THE CHAPTER, THE LAST THING I WANT TO DO IS TRIGGER SOMEONE.   
> THIS CHAPTER CONTAINS A RAPE FANTASY/RAPE PLAY, DO NOT READ IF THIS TRIGGERS YOU.

Chapter 18

Negan’s P.O.V

Roxy was due round soon. Today was the day I had decided we would try out the rape roleplay. We had planned everything out. Yet I still didn’t feel right. Even with all the planning. I’d made sure she was wearing clothes she didn’t mind getting torn and to make it realistic she was allowed to hit me anywhere that could be covered with clothes. We’d even planned out the damn scenario. She was coming round to pick up some paper work, the door would be unlocked and I would make a move on her in the kitchen. I was hiding in the hallway now, waiting for her arrival. She wanted this and she was comfortable with this. I could do this. 

I heard the door open and she called out for me. I took a deep breath to prepare myself, not responding as part of the act. I heard her move further into the house, her feet padding across the kitchen tiles. I forced myself forward and into the kitchen, coming up behind her. I pinned her against the counter with my own body, kissing the back of my neck. She froze before trying to free herself. It mainly resulting in her squirming and rubbing her ass against my crotch.   
“What are you doing? Get off of me!” She snapped.  
I had to keep reminding myself that all part of the act and that this is what she wanted. I wrapped a hand around her neck, squeezing a little. She instantly stopped squirming.

“You know what I’m doing, I’ve seen the way you look at me in the office. This is what you want,” I replied.  
I noticed how Roxy’s breathing had become deeper in arousal. As if snapping herself out of her thoughts she decided to put up more of a fight, pushing us both backwards and pulling my hand from her neck.  
“I don’t know what the fuck your talking about but you fucking touch me!” She spat.   
She made her way over to the door and I chased after her, wrapping my arms around her waist and picking her up off the floor. She screeched, kicking and batting at my arms with her fists.  
“Put me down!” 

I ignored her, carrying her with a little difficulty to the bedroom.   
“Stop struggling. We both know you want this. Why else would you fucking come to my home in that slutty little skirt?” I spoke, “I bet your pretty panties are soaked right now. If I’m wrong then you can go. But if I’m right…” I trailed off.   
Roxy froze as one of my hands went up her skirt, feeling her through her panties. Of course, she was wet.   
“Looks like you want this as much as I do,” I chuckled.  
She started struggling and protesting again. I continued our journey to the bedroom, throwing her on the bed and closing the door behind me. 

“You had your chance to leave, now that we’re in here I can do whatever I want to you,” I explained.  
Roxy attempted to make a run for the door, hoping to push past me. I grabbed her once more, shoving her back down on the bed and climbing on top of her. I had some cuffs already attached to the bedposts as to restrain her quickly. I took hold of one wrist and secured it. Now she really wouldn’t be able to go anywhere. But now this was starting to feel even more wrong. I paused, looking over her. She met my gaze, breathing heavily as she continued to tug on the restraint. I forced myself back into it, leaning down to kiss and bite at her neck. Her back arched a little and she let out a soft whine. 

“See, you know daddy can make you feel good. You just have to stop fighting,” I continued.   
As if snapping her out of the pleasure she kicked at me once again. I put more of my weight on her, stopping her from kicking. I reached down and tore her blouse open, buttons flying in all directions. Underneath she was wearing a red lacy bra. An expensive one that I’d brought her.   
“Your even wearing slutty underwear for me,” I said.   
“Fuck you!” She spat.  
“No baby girl, that’s what I’m going to do to you.”  
I yanked her skirt down before tearing her panties from her. To stop her from mouthing off I shoved her panties in her mouth as a makeshift gag. 

I restrained her other wrist and climbed off the bed to undress myself. She brought her legs up as a form of protection. I went to take my shirt off and paused once more, looking over her. No. I couldn’t do it. I knew she was going to be disappointed. But I really couldn’t do this to her no matter how much she was into it. I moved back over to her and freed both her wrists before removing her panties from her mouth. She frowned, sitting up clearly confused. I sat down on the edge of the bed, unable to look at her, at her disappointment.   
“Negan, what’s wrong?” She asked, her voice cautious.  
I put my head in my hands, frustrated with myself.  
“I can’t do this, I’m sorry. I know it’s something you were looking forward to but I just can’t,” I apologized.

Roxy fell silent for a few moments before speaking, “its ok. Don’t worry about it.”  
I got to my feet, “no its not fucking ok! I’ve pushed you to do shit that I wanted to do and I can’t do this one fucking thing. I’m meant to be some sort of fucking master at kinky shit, you have expectations of me and if I can’t live up to them then what fucking good am I?” I was shouting at this point.  
“Negan. Its ok honestly. It’s not that big of a deal, please calm down.”  
She followed me, wrapping her arms around my waist and hugging me from behind. I didn’t deserve this or her. This was the same fucking level as embarrassing as not being able to get it up. The one thing I’m meant to be good at, I guess I was losing my touch after all. 

Roxy attempted to get me to turn round so that I was facing her. I refused to budge. She’d look at me with the same discontent that Lucille did. I couldn’t face that. This was over. I felt myself go into panic mode. I had to end this. I couldn’t risk her breaking my heart like that. I couldn’t deal with that again. I took her hands and pulled them off of me.   
“I just need you to go ok. I shouldn’t have dragged you into this. Please just go,” I spoke, defeated.  
Roxy came round so that I had to look at her, “what the fuck are you talking about?”  
“I’m sorry. I’ll pay you in full for this last time. I understand if you want to quit your job after this,” I still refused to look at her.  
“What? No. Negan, please. Talk to me,” her voice cracked as she did her best to hold back tears. 

“Just go!”  
Roxy froze, never having heard me shout before. She quickly gathered her things and left the bedroom, slamming the door behind her. I waited, listening for the front door to close and her car to start up. I finally relaxed when I heard her drive off. I’d make sure to give her some good references for any future jobs. I know that I wouldn’t be able to face her at work Monday. Time to think of an excuse.


	19. Chapter 19

Chapter 19

Roxy’s P.O.V

Monday arrived and I forced myself into work, hoping to see Negan. I’d given him time to calm down so hopefully we would be able to talk now. I was afraid he really had cut things off with me though all for a misunderstanding. If anything, I would rather he stopped when he did before pushing himself to do something that he wasn’t comfortable with. That’s what safe words were for. I wanted to see if he was ok, it must have really struck a nerve with him and his feelings were more important than my kinks. I guess I put a little more effort in how I looked today, tying my hair back and wearing a red dress he’d brought me. I sat down at my desk and was greeted by Dwight.   
“Today is gonna the start of a good week,” he stated.  
“And whys that?”  
“Boss man isn’t here, took the week off.”

I felt my heart sink, well there goes any hope of talking to him face to face. I didn’t really want to corner him at his home, that’s even if he would let me inside. It would be a last resort. I pulled my phone from my bag and opened up a new message. I stared at the screen for a little while. I didn’t know what to say. It was unlikely he would answer his phone if I called him even though it would be better for me with all the things I had to say. But he didn’t have the choice to completely ignore a text. He’d read it, it was up to him if he responded or not. I just hope he did. I wanted us to move things forward and instead I’d completely freaked him out.   
_I’m sorry that I upset you Saturday, that was never my intention. I feel awful for what happened and I need to talk to you. I understand if you don’t want to see me but please just respond or call me. Please._

I hit send and waited, staring at my phone and hoping it would alert me for a text within the next few minutes. Nothing. I sighed, placing it on my desk next to my mouse and keyboard. I forced myself to work, occasionally glancing at my phone and pressing the home button in the hopes of seeing a text from him, but no such luck. Just keep working, don’t keep worrying about him or you’ll start to over think, I kept telling myself. I needed to speak to someone about this, someone who was an outsider. An outside opinion was always better than an inside opinion. I scrolled through my contacts. Chloe might be able to help, she was always good with advice or she’d try her best to give some and regardless of the situation she would always be there. That’s what counts as a good friend. 

Gwen and I had split apart. I had begun to notice some toxic things about her and I couldn’t continue to be friends with her like that. I cut her out, she didn’t even fight for me. That’s the part that hurt the most, to know that our years of friendship had meant nothing to her. Losing a close friend was like going through a breakup. Some days were better than others. I text Chloe, asking if she was free for my lunch break. A few seconds later she got back to me saying she was. Thank god for that. We decided to go for sushi, one of her favourite things to eat. Chloe was an illustrator and lived in a small apartment like my own. Only hers was decorated in all kinds of ways. She could never decide what colour to paint most of her rooms. One time she’d painted the walls blue and painted on her own little white clouds. The week after she’d painted over it with red. 

We met up at the sushi bar, exchanging hugs and kisses on the cheek. Chloe’s hair was blonde and short, coming just above her shoulders. She was wearing torn jeans, paint covered trainers and an oversized grey jumper. She was a little shorter than me and a little chubby, not that it bothered her. We sat down at a booth and ordered.   
“So, what’s up? I know that look,” she asked.  
I smiled softly, she always had a way of knowing when I wasn’t right.   
“It’s a long story,” I started.  
“Then get going, you only have an hour’s lunch break.”  
I began telling her about Negan and our arrangement. I even told her all about the fetish clubs before telling her about last Saturday without disclosing what kink it was we tried. Only Negan got to know that.

She listened intently, resting her chin in the palms of her hands. She allowed me to finish before speaking. At this time lunch had arrived and we tucked in.   
“Did you try telling him your feelings for him?” She asked.  
“Obviously not. He’s older than me, in a completely different league to me. He could do way better than me.”  
Chloe shot me a look that said, ‘bitch please’, “if that were true he wouldn’t have wanted you to be his sugar baby.”  
Well I guess she was right there.   
“Keep trying to call him. If that doesn’t work then your gonna have to go round there, unless he comes into the office. You two have to talk this out and he needs to understand. No chickening out either about your feelings, you tell that man how you feel.”

I sighed, “I know. I was just hoping you might tell me something different from what I’ve been telling myself.”  
“Also, does he happen to have a friend that’s looking for a sugar baby? I could do with someone paying my bills for me,” she joked.  
“I’ll have to look into it for you.”  
We paid for our food before exchanging more hugs and goodbyes as I had to eventually head back to work. I checked my phone for a text from him. Still nothing. I called him, holding the phone to my ear. I waited, still feeling disappointment as his answer phone message began to play.   
“Negan, please talk to me. I can’t tell you how sorry I am for what happened Saturday. Just please call me back. I miss you,” I spoke. 

I pressed the hang up button and sat back down at my desk. I don’t think I’d be able to wait till he came back into the office to try and talk to him. And going to his home would not be fair on him. Whilst I wanted him to talk to me now, I knew he had to be ready himself. Maybe there was someone on his end that could help out. I loaded up Chrome on my phone and searched for Simons club. Last thing I needed was to have someone walk past and see a fetish site on my work computer. I scrolled down to the contacts and found the clubs number. I really hope he was there. I left my booth and headed to the break room, which was thankfully empty. I dialled the number and pressed call. The phone answered on the third ring.   
“Hello?” He answered.  
“Simon, its Roxy.”  
“You ok, you sound rushed?”

“I’m not supposed to be calling you right now kinda meant to be working, but it’s important. Has Negan told you what happened Saturday?”   
“No? Something bad by the sounds of it?”  
“I don’t have time to explain it and he isn’t answering my texts or calls. Would you please go round and see if he’s ok? And maybe convince him to talk to me?”  
“Well that depends what you did of course. If he tells me you turned in to a psycho bitch like his ex then we’re gonna have issues and you can go fuck yourself.”  
“What? No. What are you talking about?”  
“Jeez, seems like both of you suck at communication. Look swing by the club when you finish work and you can tell me what happened and I can explain his situation to you.”  
“Ok, thanks Simon.”

I hung up and headed back to my desk, hoping nobody would call me out for not working. Although it seemed unlikely with Negan not in for the week. Everyone was much more relaxed and bending the rules a little. I continued to glance at the clock hoping time would go by faster…although I’m sure nobody would mind if I left maybe half an hour early. Oh, fuck it, it’s not like my boss was here to fire me for leaving work early anyway. I got up from my desk, gathered my coat and made up an excuse about a family emergency. They brought it and let me leave. I headed straight to the club, knowing I’d need to go to back door. I knocked and a few moments later Simon let me in.   
“I didn’t expect you to finish so soon,” He spoke.  
“I don’t, I’m just worried about him.”

Simon led me over to the bar, sitting down next to me on a stool. I told him about Saturday, hoping he wouldn’t ask what kink we had tried out. Although by the look on his face he could already tell. I guess he knew Negan better than anyone so why wouldn’t he know?   
“He didn’t tell you how he felt huh? Fucking chicken shit asshole,” he cursed.  
I frowned, “what do you mean?”  
“He came in here the other week looking like a lost puppy. I don’t like the fact I’m the one who has to tell you this when he should have done it himself but…the big guys got some feelings for you,” Simon explained.  
“He what? He like, like likes me?”  
“Probably not if your gonna talk like a damn fifth grader. But yeah he’s crushing on you hard.”

I felt my cheeks begin to burn and my heart felt like it was gonna beat out of my chest. Well thank god, the feeling was mutual. This would make telling him so much easier now.   
“As for why he freaked out. What you asked for, it’s something he’s very against in real life situations and struggles to take it to a bedroom situation. Not saying you’re at fault here, he should have said something if he wasn’t comfortable but knowing him he didn’t want to disappoint you.”  
“He wouldn’t have. I get it.”  
“I know that. He doesn’t. His ex-girl was a piece of shit, liked toying with his emotions, turned into a real psycho. She fucked him up real good. He hasn’t had a real relationship since. Its why he became a sugar daddy.”  
I suddenly felt super protective of Negan, like if I ever met that ex of his, I’d probably beat the shit out of her. 

“He’s scared to fall in love again because he’s scared to get hurt again. I told him you’re not the heart-breaking type but he’s still to chicken shit,” Simon continued.  
“Would you be able to get him here? So that I could talk to him, I feel like he’ll only listen to you.”  
“You want me to get my little bow and arrow too? I don’t play Cupid for free ya know,” he joked.  
Simon pulled his phone out of his pocket and sent a text to Negan. Fingers crossed he answered.


	20. Chapter 20

Chapter 20

Negan’s P.O.V

My phone buzzed, signalling a text. I glanced at it, noticing it was from Roxy. I sighed. Well at least she hadn’t called me. I gave in a read the text.  
_I’m sorry that I upset you Saturday, that was never my intention. I feel awful for what happened and I need to talk to you. I understand if you don’t want to see me but please just respond or call me. Please._  
I couldn’t do any of those things. I was afraid of what she might say. I shouldn’t have fallen for her in the first place. I only had myself to blame, I should have started to distance myself the moment I developed feelings for her. I’d rarely spent much time outside of the bedroom with my previous sugar babies, yet with Roxy I had enjoyed those moments. 

I kept telling myself that it was all a stupid crush but my heart knew better. Perhaps I could try and do something to force myself to move on from her. Find another sugar baby and quickly. Or maybe I could call one of the ex-sugar babies, take them out for dinner and back to mine for the night. Just to take my mind off Roxy. But most of them had their own lives now, own relationships that I had no right to interfere with. 

I started to get angry with myself. I couldn’t let Lucille control my thoughts and feelings anymore. Simon was right, she didn’t think of me anymore, so why should I? She’d made it clear she didn’t give a shit about me, so I needed to stop giving a shit about her. I should just pick up the phone and be honest. Tell Roxy everything, the reason I’d freaked out Saturday, how I really felt about her…but what if she laughed at me? What if she thought that it was pathetic that a guy like me was letting his ex get in the way of his happiness? I really was fucking pathetic. 

A few hours later my phone buzzed again and I assumed it was Roxy one more. Only this time I was surprised when my ringtone started playing. Great now she was fucking calling me. I continued to ignore the ringing. Until it went to answer phone. Great. I was surprised however to hear Simons voice instead of hers.  
“Negan answer your fucking phone. You can ignore Roxy all you want but I’m not gonna take that shit. If you don’t get your ass down to the club in an hour then I’m coming over and I’ll be bringing her with me. This shit is getting sorted today,” he explained.  
Just because they were coming over didn’t mean I would let them in. And like hell I was gonna go down to the bar. 

I didn’t need to be lectured by him. I poured myself a glass of Scotch and downed it quickly. It pissed me off more now that he was involved further because I knew it took a lot for him to give up. I suppose it made him a good friend, when I welcomed that kind of determination. I poured myself another glass, also downing that one quickly. I grabbed my phone and sent him a text telling him to fuck off. I just wanted to be left alone for a while. I could sort this out on my own. 

\----------------------------------------------------------------------------------------

The sun was setting and I was sat on the couch, watching TV now on my second bottle of Scotch. I’d given up on the glass as well, it was just easier to drink it from the bottle. I felt tired, like I could happily go to sleep in a matter of minutes. I heard the doorbell ring and turned to the door. I sighed and slowly got up from the couch. I made my way over to the door, making sure to take careful steps. I opened the door to find Simon stood outside. Thankfully Roxy wasn’t with him like he’d threatened. He took one look at me and gave me a disappointed look. I rolled my eyes and headed back to the couch. He followed me inside, closing the door behind him.

“So, your just gonna wallow in self-pity instead of sorting your problems?” He asked, folding his arms over his chest.  
“Yep.”  
He rolled his eyes, “how much have you drank?”  
“Enough.”  
“You gonna continue to give me one-word responses like a five-year-old or are you gonna speak to me?”  
“I didn’t want you here.”  
“Well tough shit, I’m here. It’s what friends do.”

Simon sat down next to me and took the bottle from me, putting it on the coffee table. He made sure it was out of arms reach just in case.  
“She wants to talk to you, you can’t keep ignoring her for something that wasn’t her fault,” he spoke.  
“She shouldn’t have gotten you involved.”  
“Why? Because you know I’m right, and you just hate it when I prove you wrong? You’re being a stubborn asshole and making the situation worse.”  
“Go fuck yourself!”

“She came to me because she had no idea what she’d even done wrong-“  
“What the fuck are you saying?”  
“I told her about Lucille-“  
I felt my panic and anger levels rise. He had no fucking right to tell her. it was nothing to do with either of them. Now she probably did want nothing to do with me.  
“Relax. She took it well, if anything she wanted to punch Lucille in the face. She had that psycho look in her eyes for a second,” Simon explained.  
“Wait…she…”  
“Yeah she took it well. Do I need to say it a third time? She didn’t think it was weird or stupid if that’s what you’re thinking.”

I felt a huge weight lift off my shoulders. As if all my problems in that moment had been solved. I had to see her. I got to my feet, stumbling and almost falling over them. Simon caught me, making sure I was ok.  
“If your gonna see her your gonna wanna sober up a bit, big guy,” He smirked.  
It almost seemed as if this moment were some romance movie, where everything was going to work out fine, it always was. I finally got to have my happy ending. And it was all thanks to that mustachio bastered standing next to me. I could kiss him right now. Simon sat me down in the kitchen and got me some water as well as some food. I drank and ate quickly, eager to see her. 

Simon made a call, telling her to meet at the club in an hour. I continued drinking plenty of water, slowly starting to feel more awake and coherent. I went to the bedroom and changed into some clean and presentable clothes. I felt like I should buy her flowers or something but I guess there wasn’t much time. Besides if things did continue to turn out like a romance movie I could get her flowers every damn week if I wanted too. 

Simon wolf whistled as I went back into the kitchen. I rolled my eyes with a smirk.  
“Looking a lot better,” he commented.  
“Let’s just go.”  
He put an arm over my shoulder, leading me over to the front door.  
“You know once this is all over. You two are really gonna owe me. And I mean really owe me. You ever considered being a main attraction at the club?” He smirked.  
“Simon,” I spoke calmly, “fuck off.”  
He laughed, “I thought I’d get that answer. Not that it matters, every time you two do something out on the main floor you end up the main attraction.”

\----------------------------------------------------------------------------------------

We arrived at the club and headed inside. We were a little early but that gave me time to prepare what I would say to her. I glanced at the clock and no sooner had I done that the doorbell for the back door rang. She was here. I took a deep breath to calm myself, I felt so nervous. Simon went to the door to let him in, leaving me at the bar area. Roxy and Simon made their way back into the main room, a silence falling over the three of us.  
“Well, I’ve got some shit out back to do,” Simon announced before leaving the two of us alone.  
I cleared my throat, nervous of what to say or do. I just wanted everything to go back to the way it was. 

I opened my mouth to speak but Roxy pulled me into a hug. I accepted, wrapping my arms around her and holding her close. I smiled, stroking her hair and kissing the top of my head. I had missed this. Missed her.  
“I’m sorry baby girl,” I spoke.  
“I’m sorry too, daddy.”  
I cupped her cheek and leaned down to kiss her softly. She kissed me back before resting her forehead against mine.  
“If I’d had known I never would have asked,” she continued.  
“I know. I should have said something sooner instead of risking losing you.”

“You could never lose me. I want to be with you Negan. I don’t want to be paid to love you anymore. You never needed to pay me in the first place.”  
I kissed her again, my fingers in her hair.  
“Your so fucking perfect,” I spoke softly.  
She smiled, her cheeks burning a little at the compliment.  
“So how about we start things off with a proper date? Dinner tomorrow night? My treat?” I asked.  
“Hasn’t it always been your treat?”  
I smirked, “well now I have more of a reason to be a gentleman.”

We decided on a time that I would pick her up and where we would go. I wanted to spend more time with her but it was getting super late and she did have work tomorrow. I pulled her into my arms once more, savouring the feeling of having her close. I smelt her hair, smiling softly at how good it smelt. Passion fruit. I kissed the top of her head before kissing her again. Simon poked his head back in to check up on us.  
“You two kissed and made up yet?” He asked.  
“None of your fucking business,” I smirked, I turned my attention back to Roxy, “so I'll pick you up for six.”  
She smiled, practicality beaming, “I cant wait.”


	21. Chapter 21

**Summary for the Chapter:**

> This is the last chapter you guys, I hope you enjoyed reading. Thank you to all that stuck with this, left comments, kudos and bookmarks. Your feedback means the world to me. 
> 
> This is not the end of this AU however. There will be someone one shots in the future with some more sexy escapades. 
> 
> Thank you again :D

Chapter 21

Roxy’s P.O.V

I practically raced home from work the next day, desperate for as much time as possible to get myself ready. I jumped into the shower, dousing myself in orange body wash. I washed my hair and got out the shower, glancing at the clock to see how much time I had left. An hour. I dried my hair and put some loose curls into it. I then began rifling through my wardrobe for something nice to wear. The only nice things I really had were things he’d brought for me. I picked out a red strapless lacy dress. I found some plain black heels and a purse to go with it. I sat down at my dressing table and gave myself a simple makeup look, opting for dark red lipstick to go with the dress. 

I was looking myself over in the mirror making sure I looked perfect as the doorbell rang. Shit he was here already. Well at least he was on time, I couldn’t fault him for that. I smiled at myself and headed to the door. I opened it and smiled wide at the sight before me. Negan was dressed in a black suit, the top two buttons undone and no tie so he looked a little casual. He was holding a huge bunch of red roses. I took them from him and kissed him on the cheek.  
“Thank you, you didn’t have too,” I spoke.  
“It’s our first proper date as a couple. I gotta do all the cliché things,” he replied.  
I smiled and let him in, whilst I put the flowers in some water. Once I knew they would be ok whilst we were out we left the apartment. Negan slipped his hand in mine, lacing his fingers with my own. 

“You look fucking beautiful tonight baby girl,” he spoke.  
“I’m glad you think so. I didn’t put all this effort in for nothing,” I smirked.  
He kissed my cheek and squeezed my hand as he led me to the car. He opened the door for me, letting me in. I sat down and buckled up. He climbed into the driver’s seat and started the engine. I had no idea where we were going for dinner but I knew Negan wouldn’t disappoint. Part of me hoped we would be going back to his tonight. 

We arrived at a fair-sized restaurant called ‘The Continental’ and were seated in a cosy booth near the back. We both looked over the menu. The food provided wasn’t too fancy nor was it too cheap. It was a middle ground place and I liked that. He wasn’t showing off how much money he had by taking me to the most expensive place in town that sold edible gold.  
“You ever had oysters?” I asked him.  
“Nope, why?”  
“Just curious, I’ve never had them and wanted to try them. Their supposed to be an aphrodisiac,” I winked at the last part.  
Negan smirked, “that so?”  
“Mhm.”

“Alright we’ll share some of those, but we’ll get some bread just in case we don’t like them.”  
“Good idea.”  
We continued to look through the menu, choosing our main courses. I decided on a steak, Negan chose a burger. A waiter took our orders, coming back shortly after with a bottle of wine.  
“So now that we’re an official couple what does that mean for work?” I asked.  
“That’s up to you. Any decision you make, I want it to be something you’re comfortable with.”  
“Well I’m not sure. I don’t know how I’d feel if everyone knew I was dating my boss. any promotion I might get would seem biased.”  
“Who says you’re getting a promotion?” He smirked.  
“Well I’m just hypothetically, if I were to get a promotion they would see it as biased, that I’m only getting it because I’m with you.”

“Then what would you rather do?”  
“It was only an internship at your place. I should probably quit. I gotta keep you excited to see me after all.”  
“Where would you go?”  
“I don’t know yet, any suggestions?”  
“I’m more than happy to help you find something you’d be happy with and I can give you a glowing reference.”  
“I’m sure you can. I obviously have great oral skills,” I joked.  
Both of us laughed at this. the waiter came back with our starters, we both looked at the oysters, seeing who was going to go first. Neither of us made a move for one. 

“We’ll do it together on three,” Negan decided.  
We both picked one up, looking at each other. We counted down, raising the shell to our lips. On three we both attempted to down them like you would a shot. I cringed at the taste wanting to spit the food out but I had no choice but to swallow. Negan seemed to be in the same predicament. We coughed and cringed, both going for our drinks and taking quick mouthfuls to get rid of the taste. They really were that awful. We both met each other’s gaze and fell about laughing again. This was nice, I hadn’t laughed like this in a long time. Nor had I enjoyed a date this much in a long time. 

\--------------------------------------------------------------------------------------------------------------------------

Negan paid the bill after we finished dessert. I wanted to go back to his place, I wanted him to take me back there and make love to me. Negan took my hand in his and pressed his lips to my knuckle.  
“You wanna come back to my place baby girl? Or should we continue with typical date tradition and wait until the third date?” He asked.  
“Since when has our relationship been traditional?” I smirked.  
He took this as my answer and led me back to the car before driving us back to his place. He led me inside and the second he closed the front door we were on each other. We kissed each other hard, holding each other close. 

He picked me up wedding style and carried me to his bedroom, placing me down on the bed. He leaned down to kiss me, removing his jacket and unbuttoning his shirt. I guessed he’d missed me that much. Good because I sure as hell had missed him too. I kicked off my heels and began pulling off my dress. Negan looked at my choice of underwear and grinned.  
“Eager baby girl?” He asked.  
“Of course.”  
“Had this all planned out?”  
I nodded, pulling him down for another kiss. It felt like I hadn’t kissed him in years. Negan climbed on top of me, kissing and nipping at my neck. He continued his journey south, kissing over every piece of me he could. 

He took the waistband of my panties between his teeth and pulled them down my thighs. I bit my lip, feeling desire run through my, the area between my legs now throbbing with need. Fucking show off. He made his way back up to my lips, reaching round and unclasping my bra with one hand and he did it the first time too.  
“You don’t need to show off daddy, we both know how skilled you are in this department,” I giggled.  
“I just wanna show my baby girl a good time.”  
“You always do.”  
I pulled his boxers off and wrapped my legs around his waist. He rubbed the head of his cock against my wetness, both of us breathing heavily. I moaned softly as he rubbed over my clit. My hips bucked, desperate for him. 

Eventually after enough teasing he pushed himself inside of me. We both moaned at the missed feeling, his forehead resting against mine. I wrapped my arms around him, pressing my lips to his again.  
“Fuck I’ve missed you baby girl,” he groaned.  
“I’ve missed you too daddy.”  
He started a slow pace, rolling his hips against mine. I did the same to increase the friction. It wouldn't take me long to cum like this, not with my clit constantly being stimulated. I gripped his forearms, my nails digging into his skin as I moaned his name. 

Negan sped up the pace a little, determined to make me moan louder, determined to make me cum. I threw my head back as he started to mark up my neck, moaning against me. I could already feel my orgasm building from the constant stimulation on my clit. Good thing I planned on staying the night. I wanted to go for a few more rounds first, make up for the sex we’d missed.  
“Cum for me baby girl,” he managed.  
Negan himself looked like he was doing his best to hold himself together. His teeth were grit together, some of his hair had come loose and hung in front of his forehead which was slightly damp with sweat and the veins in his neck were starting to become more prominent. 

My nails dragged down his back, likely leaving red marks. Finally, practically screaming his name I reached my first climax of the evening. My walls clenched around him, throwing him into his own orgasm. He let out a string of curses, his pace speeding up once more as he rode out of the waves of his orgasm. Finally, both of us stilled, breathing heavily and kissing each other. He lay down next to me and pulled me into his arms, kissing my temple.  
“I don’t think I’ll ever get bored of that,” I spoke.  
“I should fucking hope not,” he chuckled, “now what time is it you start work tomorrow?”  
“9am, like always.”  
“You better make sure you’re not late, don’t wanna piss off your boss,” he smirked.  
“I’m sure I can make up for it by putting in some over time if need be.”  
We smiled at each other, happy to be in each other’s company and to finally be together. I couldn’t think of a happier ending.


End file.
